Compound characterization data — Brägger et al., 2026

Y. Brägger, E. Tufano, P. Gärtner, A.-S. K. Paschke, D. T. Egger, L. Sorrentino, M. C. Amberg, B. Morandi. “Modular synthesis of rare N-heterocycles by nitrogen insertion into allylic nucleophiles.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007432/v1

4-Methyl-N-(2-methylallyl)benzenesulfonamide
¹H NMR (500 MHz, CDCl₃)	δ 7.75 (d, J = 8.3 Hz, 2H), 7.32 – 7.28 (m, 2H), 4.88 – 4.78 (m, 2H), 4.61 (t, J = 6.6 Hz, 1H), 3.51 – 3.45 (m, 2H), 2.43 (s, 3H), 1.68 (dd, J = 1.4, 0.8 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 143.6, 140.6, 137.1, 129.8, 127.3, 112.9, 49.2, 21.7, 20.2
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₁H₁₅NNaO₂S 248.0716; Found 248.0711

tert-Butyl (2-methylallyl)carbamate
¹H NMR (500 MHz, CDCl₃)	δ 4.92 – 4.79 (m, 2H), 4.64 (s, 1H), 3.65 (s, 2H), 1.72 (dd, J = 1.5, 0.8 Hz, 3H), 1.45 (s, 9H)
¹³C NMR (126 MHz, CDCl₃)	δ 156.1, 142.8, 110.5, 79.5, 46.4, 28.5, 20.3
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₉H₁₇NNaO₂ 194.1151; Found 194.1151

Benzyl (2-Methylallyl)carbamate
¹H NMR (500 MHz, CDCl₃)	δ 7.41 – 7.28 (m, 5H), 5.12 (s, 2H), 4.94 (s, 1H), 4.86 (tt, J = 2.1, 0.9 Hz, 1H), 4.84 (dt, J = 2.6, 1.3 Hz, 1H), 3.74 (d, J = 6.2 Hz, 2H), 1.74 (s, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 156.5, 142.2, 136.7, 128.6, 128.2, 110.8, 66.9, 46.8, 20.3
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₂H₁₅NNaO₂ 228.0995; Found 228.0992

(9H-Fluoren-9-yl)methyl (2-methylallyl)carbamate
¹H NMR (500 MHz, CDCl₃)	δ 7.77 (dt, J = 7.6, 1.0 Hz, 2H), 7.61 (d, J = 7.5 Hz, 2H), 7.41 (tt, J = 7.5, 0.9 Hz, 2H), 7.32 (td, J = 7.5, 1.2 Hz, 2H), 4.90 (t, J = 6.3 Hz, 1H), 4.84 (t, J = 1.4 Hz, 2H), 4.45 (d, J = 6.9 Hz, 2H), 4.24 (t, J = 6.9 Hz, 1H), 3.75 (d, J = 6.2 Hz, 2H), 1.74 (s, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 156.5, 144.1, 142.3, 141.5, 127.8, 127.2, 125.1, 120.1, 110.9, 66.7, 47.4, 46.8, 20.3
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₉H₁₉NNaO₂ 316.1308; Found 316.1307

N-(2-(((tert-butyldimethylsilyl)oxy)methyl)allyl)-4-methylbenzenesulfonamide
¹H NMR (400 MHz, CDCl₃)	δ 7.77 – 7.67 (m, 2H), 7.33 – 7.27 (m, 2H), 5.06 (qt, J = 1.4, 0.7 Hz, 1H), 4.96 (h, J = 1.1 Hz, 1H), 4.71 (d, J = 6.5 Hz, 1H), 4.05 (t, J = 1.2 Hz, 2H), 3.59 (d, J = 5.9 Hz, 2H), 2.43 (s, 3H), 0.87 (s, 9H), 0.03 (s, 6H)
¹³C NMR (101 MHz, CDCl₃)	δ 143.6, 143.4, 137.0, 129.8, 127.3, 113.3, 65.1, 46.2, 26.0, 21.7, 18.4, -5.3
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₇H₃₀NO₃SSi 356.1710; Found 356.1702

tert-Butyl (2-(((tert-butyldimethylsilyl)oxy)methyl)allyl)carbamate
¹H NMR (500 MHz, CDCl₃)	δ 5.10 (q, J = 1.4 Hz, 1H), 4.99 (q, J = 1.3 Hz, 1H), 4.77 (s, 1H), 4.14 (d, J = 1.3 Hz, 2H), 3.75 (d, J = 6.0 Hz, 2H), 1.44 (s, 9H), 0.91 (s, 9H), 0.07 (s, 6H)
¹³C NMR (126 MHz, CDCl₃)	δ 156.0, 145.6, 111.0, 79.4, 65.0, 43.3, 28.5, 26.0, 18.5, -5.3
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₅H₃₁NNaO₃Si 324.1965; Found 324.1963

N-(4-Sulfamoylphenyl)acetamide
¹H NMR (400 MHz, d₆-DMSO)	δ 10.26 (s, 1H), 7.81 – 7.64 (m, 4H), 7.23 (s, 2H), 2.08 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 168.9, 142.2, 138.1, 126.7, 118.4, 24.1
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₈H₁₀N₂NaO₃S 237.0304; Found 237.0304

N-(4-(N-(2-Methylallyl)sulfamoyl)phenyl)acetamide
¹H NMR (400 MHz, DMSO)	δ 10.29 (s, 1H), 7.80 – 7.62 (m, 5H), 4.87 – 4.65 (m, 2H), 3.28 (s, 2H), 2.08 (s, 3H), 1.69 – 1.55 (m, 3H)
¹³C NMR (101 MHz, DMSO)	δ 169.0, 142.7, 141.2, 134.4, 127.6, 118.5, 111.8, 48.2, 24.1, 19.9
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₂H₁₆N₂NaO₃S 291.0774; Found 291.0773

N-(2-Methylallyl)-4-(5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide
¹H NMR (500 MHz, CDCl₃)	δ 7.90 – 7.77 (m, 2H), 7.52 – 7.40 (m, 2H), 7.21 – 7.15 (m, 2H), 7.13 – 7.05 (m, 2H), 6.74 (d, J = 0.6 Hz, 1H), 4.88 – 4.77 (m, 2H), 4.67 (t, J = 6.4 Hz, 1H), 3.51 (dtd, J = 6.4, 1.2, 0.5 Hz, 2H), 2.38 (d, J = 0.8 Hz, 3H), 1.67 (dd, J = 1.5, 0.9 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 145.4, 144.2 (q, J = 38.6 Hz), 142.6, 140.3, 139.9, 139.6, 129.9, 128.9, 128.2, 125.8, 125.7, 121.2 (q, J = 269.1 Hz), 113.2, 106.4 (q, J = 2.0 Hz), 49.2, 21.5, 20.2
¹⁹F NMR (471 MHz, CDCl₃)	δ -62.44
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₂₁H₂₀F₃N₃NaO₂S 458.1121; Found 458.1125

2-Chloro-5-(1-hydroxy-3-oxoisoindolin-1-yl)-N-(2-methylallyl)benzenesulfonamide
¹H NMR (400 MHz, CDCl₃)	δ 8.24 (d, J = 2.6 Hz, 2H), 7.60 (dd, J = 8.4, 2.3 Hz, 1H), 7.48 – 7.42 (m, 2H), 7.34 – 7.28 (m, 2H), 7.25 (d, J = 7.6 Hz, 1H), 5.72 (s, 1H), 5.44 (t, J = 6.4 Hz, 1H), 4.81 – 4.78 (m, 1H), 4.72 (t, J = 1.4 Hz, 1H), 3.44 (d, J = 6.3 Hz, 2H), 1.60 (t, J = 1.1 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 170.7, 149.0, 140.3, 140.2, 137.6, 133.6, 132.1, 131.6, 131.2, 130.0, 129.2, 128.4, 123.7, 122.8, 113.4, 87.8, 49.2, 20.1
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₈H₁₇ClN₂NaO₄S 415.0490; Found 415.0489

5-Chloro-2-methoxy-N-(4-(N-(2-methylallyl)sulfamoyl)phenethyl)benzamide
¹H NMR (500 MHz, CDCl₃)	δ 8.16 (d, J = 2.8 Hz, 1H), 7.85 – 7.75 (m, 3H), 7.41 – 7.37 (m, 3H), 6.88 (d, J = 8.8 Hz, 1H), 4.84 (dp, J = 12.9, 1.3 Hz, 2H), 4.46 (t, J = 6.4 Hz, 1H), 3.79 (s, 3H), 3.75 (td, J = 6.9, 5.8 Hz, 2H), 3.50 (s, 2H), 3.01 (t, J = 6.9 Hz, 2H), 1.68 (t, J = 1.1 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 164.2, 156.0, 144.9, 140.6, 138.4, 132.6, 132.1, 129.8, 127.5, 127.0, 122.8, 113.0, 113.0, 56.4, 49.2, 40.8, 35.7, 20.2
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₂₀H₂₄ClN₂O₄S 423.1140; Found 423.1138

4-(5-Methyl-3-phenylisoxazol-4-yl)-N-(2-methylallyl)benzenesulfonamide
¹H NMR (400 MHz, CDCl₃)	δ 8.02 – 7.74 (m, 2H), 7.45 – 7.27 (m, 7H), 4.90 – 4.78 (m, 2H), 4.65 (t, J = 6.4 Hz, 1H), 3.58 (d, J = 6.0 Hz, 2H), 2.49 (s, 3H), 1.68 (dd, J = 1.5, 0.8 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 167.4, 161.2, 140.5, 139.5, 135.4, 130.4, 129.9, 128.8, 128.6, 128.6, 127.6, 114.6, 113.1, 49.3, 20.2, 11.9
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₂₀H₂₁N₂O₃S 369.1267; Found 369.1268

N,N-Dimethyl-2-(N-(2-methylallyl)sulfamoyl)nicotinamide
¹H NMR (500 MHz, C₂D₂Cl₄)	δ 8.72 (dd, J = 4.7, 1.7 Hz, 1H), 7.74 (dd, J = 7.7, 1.6 Hz, 1H), 7.57 (dd, J = 7.7, 4.7 Hz, 1H), 5.40 (t, J = 6.4 Hz, 1H), 4.87 (td, J = 1.4, 0.8 Hz, 1H), 4.79 (p, J = 1.2 Hz, 1H), 3.76 – 3.43 (m, 2H), 3.12 (s, 3H), 2.87 (s, 3H), 1.67 (dd, J = 1.5, 0.8 Hz, 3H)
¹³C NMR (126 MHz, C₂D₂Cl₄)	δ 167.6, 153.5, 149.0, 140.6, 136.0, 131.9, 126.1, 112.5, 49.3, 38.8, 35.0, 19.8
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₂H₁₇N₃NaO₃S 306.0883; Found 306.0883

2-(N,N-Bis(2-methyl-allyl)sulfamoyl)-N,N-dimethylnicotinamide
¹H NMR (500 MHz, C₂D₂Cl₄)	δ 8.70 (dd, J = 4.6, 1.7 Hz, 1H), 7.70 (dd, J = 7.8, 1.7 Hz, 1H), 7.52 (dd, J = 7.8, 4.6 Hz, 1H), 4.85 (t, J = 1.6 Hz, 2H), 4.83 – 4.80 (m, 2H), 4.02 – 3.77 (m, 4H), 3.09 (s, 3H), 2.81 (s, 3H), 1.55 (dd, J = 1.4, 0.8 Hz, 6H)
¹³C NMR (126 MHz, C₂D₂Cl₄)	δ 166.9, 153.6, 149.4, 139.9, 136.3, 131.7, 126.4, 114.5, 53.2, 38.6, 34.9, 19.8
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₆H₂₃N₃NaO₃S 360.1352; Found 360.1354

N-(2-Methylallyl)-4-(m-tolylamino)pyridine-3-sulfonamide
¹H NMR (500 MHz, CDCl₃)	δ 8.74 (s, 1H), 8.25 (d, J = 6.0 Hz, 1H), 8.05 (s, 1H), 7.31 – 7.26 (m, 1H), 7.05 (ddt, J = 7.6, 1.8, 0.8 Hz, 1H), 7.00 – 6.97 (m, 2H), 6.94 (dd, J = 6.0, 0.5 Hz, 1H), 5.57 (t, J = 6.3 Hz, 1H), 4.90 – 4.76 (m, 2H), 3.57 (d, J = 4.9 Hz, 2H), 2.36 (d, J = 0.8 Hz, 3H), 1.67 (dd, J = 1.5, 0.8 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 153.4, 150.9, 149.4, 140.3, 140.1, 137.8, 129.7, 127.0, 124.6, 120.9, 119.2, 113.2, 108.5, 49.0, 21.5, 20.1
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₆H₂₀N₃O₂S 318.1271; Found 318.1269

N-(2-Methylallyl)-1-(2-(trifluoromethyl)phenyl)methanesulfonamide
¹H NMR (500 MHz, CDCl₃)	δ 7.76 – 7.68 (m, 1H), 7.60 (td, J = 7.7, 1.4 Hz, 1H), 7.49 (tt, J = 7.6, 1.1 Hz, 1H), 4.87 (dp, J = 9.2, 1.3 Hz, 1H), 4.52 (s, 1H), 3.50 – 3.35 (m, 1H), 1.78 – 1.64 (m, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 141.1, 133.2, 132.2 (q, J = 1.1 Hz), 129.8 (q, J = 30.0 Hz), 129.0, 127.8 (d, J = 1.7 Hz), 126.7 (q, J = 5.5 Hz), 124.2 (q, J = 274.0 Hz), 112.9, 55.8 (q, J = 2.1 Hz), 49.5, 20.1
¹⁹F NMR (377 MHz, CDCl₃)	δ -58.15
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₂H₁₅F₃NO₂S 294.0770; Found 294.0770

N-(2-Methylallyl)thiophene-2-sulfonamide
¹H NMR (400 MHz, CDCl₃)	δ 7.70 – 7.45 (m, 2H), 7.17 – 6.96 (m, 1H), 4.87 (d, J = 13.0 Hz, 2H), 4.71 (t, J = 6.3 Hz, 1H), 3.58 (d, J = 6.2 Hz, 2H), 1.71 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 141.1, 140.3, 132.3, 132.0, 127.5, 113.1, 49.4, 20.2
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₈H₁₂NO₂S₂ 218.0304; Found 218.0304

((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl (2-methylallyl)sulfamate
¹H NMR (500 MHz, CDCl₃)	δ 4.99 – 4.91 (m, 2H), 4.62 (dd, J = 7.9, 2.6 Hz, 1H), 4.59 (t, J = 6.3 Hz, 1H), 4.33 (d, J = 2.6 Hz, 1H), 4.24 (ddd, J = 7.9, 1.9, 0.8 Hz, 1H), 4.22 (d, J = 10.5 Hz, 1H), 4.15 (d, J = 10.6 Hz, 1H), 3.91 (dd, J = 13.0, 1.9 Hz, 1H), 3.76 (dd, J = 13.0, 0.8 Hz, 1H), 3.71 – 3.68 (m, 2H), 1.79 (dd, J = 1.4, 0.8 Hz, 3H), 1.55 (d, J = 0.7 Hz, 3H), 1.47 (d, J = 0.7 Hz, 3H), 1.42 (d, J = 0.7 Hz, 3H), 1.34 (d, J = 0.7 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 140.4, 113.4, 109.4, 109.4, 101.0, 70.8, 70.4, 70.4, 70.1, 61.5, 49.8, 26.6, 26.0, 25.3, 24.2, 20.3
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₆H₂₇NNaO₈S 416.1350; Found 416.1350
Optical rotation	[α]28.9_D = -32.3 (c = 1.33, CHCl3)

N-(2-methylallyl)quinoline-8-sulfonamide
¹H NMR (500 MHz, CDCl₃)	δ 9.02 (dd, J = 4.3, 1.8 Hz, 1H), 8.43 (dd, J = 7.3, 1.5 Hz, 1H), 8.31 (dd, J = 8.3, 1.8 Hz, 1H), 8.07 (dd, J = 8.2, 1.5 Hz, 1H), 7.66 (dd, J = 8.2, 7.2 Hz, 1H), 7.57 (dd, J = 8.3, 4.3 Hz, 1H), 6.47 (s, 1H), 4.82 (qt, J = 1.5, 0.8 Hz, 1H), 4.75 (ddt, J = 2.5, 1.7, 0.8 Hz, 1H), 3.39 (d, J = 5.0 Hz, 2H), 1.64 (dd, J = 1.4, 0.8 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 151.3, 143.2, 140.8, 137.4, 135.9, 133.4, 131.4, 128.9, 125.9, 122.4, 112.6, 49.4, 20.4
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₃H₁₅N₂O₂S 263.0849; Found 263.0845

N-(2-Methylallyl)pyrimidin-2-amine
¹H NMR (400 MHz, CDCl₃)	δ 8.28 (d, J = 4.8 Hz, 2H), 6.54 (t, J = 4.8 Hz, 1H), 5.52 (s, 1H), 4.97 – 4.78 (m, 2H), 4.06 – 3.92 (m, 2H), 1.79 (dq, J = 1.5, 0.7 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 162.6, 158.2, 142.8, 110.8, 110.3, 47.0, 20.6
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₈H₁₂N₃ 150.1026; Found 150.1024

2,6-Dichloro-N-(2-methylallyl)pyrimidin-4-amine
¹H NMR (500 MHz, CDCl₃)	δ 6.61 (s, 1H), 5.49 (s, 1H), 4.95 – 4.78 (m, 2H), 4.00 (ddtd, J = 6.2, 1.8, 1.2, 0.6 Hz, 2H), 1.78 (dq, J = 1.4, 0.7 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 163.3, 161.8, 141.6, 120.3, 111.2, 109.4, 47.2, 20.6
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₈H₁₀Cl₂N₃ 218.0246; Found 218.0246

2-chloro-6-methyl-N-(2-methylallyl)pyrimidin-4-amine
¹H NMR (400 MHz, CDCl₃)	δ 6.45 (s, 1H), 5.30 (s, 1H), 4.94 – 4.81 (m, 2H), 4.04 – 3.96 (m, 2H), 2.31 (s, 3H), 1.78 (dt, J = 1.5, 0.7 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.6, 162.2, 161.3, 142.4, 110.7, 109.5, 47.0, 23.9, 20.6
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₉H₁₃ClN₃ 198.0793; Found 198.0791

methyl 2-chloro-6-((2-methylallyl)amino)pyrimidine-4-carboxylate
¹H NMR (400 MHz, DMSO)	δ 8.49 (t, J = 5.9 Hz, 1H), 7.15 (s, 1H), 4.83 (dd, J = 2.8, 1.4 Hz, 2H), 3.91 (d, J = 5.8 Hz, 2H), 3.84 (s, 3H), 1.72 (d, J = 1.3 Hz, 3H)
¹³C NMR (101 MHz, DMSO)	δ 164.4, 163.7, 160.3, 153.2, 141.3, 110.7, 106.2, 52.7, 45.5, 20.3
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₀H₁₃ClN₃O₂ 242.0691; Found 242.0688

(2-((5-Chloro-2-((2-methylallyl)amino)pyrimidin-4-yl)amino)phenyl)dimethylphosphine Oxide
¹H NMR (400 MHz, CDCl₃)	δ 10.90 (s, 1H), 8.73 – 8.56 (m, 1H), 7.98 (s, 1H), 7.47 (ddt, J = 8.7, 7.3, 1.4 Hz, 1H), 7.30 – 7.22 (m, 1H), 7.09 (tdd, J = 7.6, 2.4, 1.1 Hz, 1H), 5.00 – 4.78 (m, 2H), 3.94 (d, J = 6.2 Hz, 2H), 1.84 (s, 3H), 1.81 (s, 3H), 1.80 (dt, J = 1.5, 0.7 Hz, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 160.1, 156.2, 154.7, 144.3 (d, J = 2.6 Hz), 142.8, 132.5, 132.4, 129.7 (d, J = 11.0 Hz), 122.5 (d, J = 7.1 Hz), 122.4 (d, J = 12.3 Hz), 120.0 (d, J = 95.6 Hz), 110.4, 47.5, 20.6, 18.8 (d, J = 71.6 Hz)
³¹P NMR (202 MHz, CDCl₃)	δ 44.33
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₆H₂₁ClN₄OP 351.1136; Found 351.1144

5-Chloro-N4-(2-(isopropylsulfonyl)phenyl)-N2-(2-methylallyl)pyrimidine-2,4-diamine
¹H NMR (400 MHz, CDCl₃)	δ 9.56 (s, 1H), 8.63 (dd, J = 8.5, 1.1 Hz, 1H), 8.02 (s, 1H), 7.89 (dd, J = 8.0, 1.6 Hz, 1H), 7.60 (ddd, J = 8.7, 7.3, 1.7 Hz, 1H), 7.21 (ddd, J = 7.9, 7.3, 1.1 Hz, 1H), 4.96 – 4.79 (m, 2H), 3.93 (d, J = 6.2 Hz, 2H), 3.23 (hept, J = 6.9 Hz, 1H), 1.82 (s, 1H), 1.79 (dq, J = 1.4, 0.7 Hz, 3H), 1.31 (d, J = 6.9 Hz, 6H)
¹³C NMR (151 MHz, CDCl₃)	δ 160.3, 155.5, 155.4, 142.6, 138.9, 134.5, 131.3, 124.3, 123.1, 122.8, 110.4, 55.6, 47.5, 20.6, 15.5
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₇H₂₂ClN₄O₂S 381.1147; Found 381.1147

5-Fluoro-4-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazol-6-yl)-N-(2-methylallyl)-pyrimidin-2-amine
¹H NMR (400 MHz, CDCl₃)	δ 8.23 (d, J = 4.0 Hz, 1H), 8.09 (d, J = 1.3 Hz, 1H), 7.78 – 7.72 (m, 1H), 5.37 – 5.20 (m, 1H), 4.99 – 4.82 (m, 2H), 4.71 (hept, J = 7.0 Hz, 1H), 4.04 (d, J = 6.1 Hz, 2H), 2.68 (s, 3H), 1.82 (dd, J = 1.5, 0.8 Hz, 3H), 1.68 (d, J = 7.0 Hz, 6H)
¹³C NMR (151 MHz, CDCl₃)	δ 159.1 (d, J = 2.2 Hz), 153.4, 153.3 (d, J = 251.2 Hz), 151.3, 150.3 (d, J = 250.7 Hz), 147.2 (d, J = 26.8 Hz), 142.8, 136.5, 133.7 (d, J = 17.2 Hz), 128.4 – 128.1 (m), 110.5, 108.7 (dd, J = 9.3, 3.5 Hz), 108.2 (dd, J = 20.0, 6.4 Hz), 48.7, 47.8, 21.6, 20.7, 15.2
¹⁹F NMR (377 MHz, CDCl₃)	δ -128.44, -153.22
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₉H₂₂F₂N₅ 358.1838; Found 358.1837

N-(tert-Butyl)-3-((5-methyl-2-((2-methylallyl)amino)pyrimidin-4-yl)amino)benzene-sulfonamide
¹H NMR (400 MHz, CDCl₃)	δ 8.25 (t, J = 2.0 Hz, 1H), 7.90 – 7.86 (m, 1H), 7.79 (s, 1H), 7.55 (ddd, J = 7.8, 1.8, 1.0 Hz, 1H), 7.42 (t, J = 8.0 Hz, 1H), 6.50 (s, 1H), 4.94 – 4.80 (m, 2H), 4.56 (s, 1H), 3.98 (d, J = 6.1 Hz, 2H), 2.09 (d, J = 0.9 Hz, 3H), 1.80 (dd, J = 1.5, 0.8 Hz, 3H), 1.25 (s, 9H)
¹³C NMR (101 MHz, CDCl₃)	δ 160.5 (resolved through HMBC), 159.2, 154.7 (resolved through HMBC), 144.0, 143.0 (resolved through HMBC), 139.9, 129.4, 123.9, 121.3, 118.8, 110.4, 103.7, 55.0, 47.3, 30.4, 20.7, 13.3
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₉H₂₈N₅O₂S 390.1958; Found 390.1957

tert-Butyl 4-(4-((2-methylallyl)amino)pyrimidin-2-yl)piperazine-1-carboxylate
¹H NMR (400 MHz, CDCl₃)	δ 7.89 (d, J = 5.8 Hz, 1H), 5.70 (d, J = 5.8 Hz, 1H), 4.98 – 4.86 (m, 2H), 4.81 (s, 1H), 3.86 (s, 2H), 3.77 – 3.69 (m, 4H), 3.49 – 3.41 (m, 4H), 1.77 (dd, J = 1.5, 0.8 Hz, 3H), 1.48 (s, 9H)
¹³C NMR (101 MHz, CDCl₃)	δ 163.1, 161.7, 156.2, 155.0, 142.2, 111.2, 94.2, 79.9, 47.0, 43.7, 28.6, 20.5
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₇H₂₈N₅O₂ 334.2238; Found 334.2236

N4-(2,3-dimethyl-2H-indazol-6-yl)-N4-methyl-N2-(2-methylallyl)pyrimidine-2,4-diamine
¹H NMR (400 MHz, CDCl₃)	δ 7.68 (d, J = 6.0 Hz, 1H), 7.57 (dd, J = 8.8, 0.8 Hz, 1H), 7.45 (dd, J = 1.8, 0.8 Hz, 1H), 6.87 (dd, J = 8.8, 1.8 Hz, 1H), 5.67 (d, J = 6.0 Hz, 1H), 5.06 (s, 1H), 4.95 (tq, J = 1.6, 0.8 Hz, 1H), 4.85 (p, J = 1.4 Hz, 1H), 4.10 (s, 3H), 4.01 (dq, J = 6.1, 0.9 Hz, 2H), 3.47 (s, 3H), 2.62 (s, 3H), 1.80 (dq, J = 1.3, 0.6 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 163.1, 162.1, 155.4, 148.1, 143.6, 143.0, 132.0, 121.2, 120.8, 119.9, 114.6, 110.3, 96.0, 47.2, 37.8, 37.6, 20.7, 10.1
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₈H₂₃N₆ 323.1979; Found 323.1975

N-(4-(4-fluorophenyl)-5-(1-hydroxy-2-methylallyl)-6-isopropylpyrimidin-2-yl)methanesulfonamide
¹H NMR (400 MHz, CDCl₃)	δ 7.64 – 7.53 (m, 2H), 7.19 – 7.09 (m, 2H), 5.33 (d, J = 3.9 Hz, 1H), 5.06 (dp, J = 2.7, 1.4 Hz, 1H), 4.89 (dt, J = 2.0, 1.0 Hz, 1H), 3.58 – 3.49 (m, 7H), 2.03 (d, J = 4.6 Hz, 1H), 1.72 (dt, J = 1.6, 0.9 Hz, 3H), 1.27 (d, J = 6.6 Hz, 3H), 1.21 (d, J = 6.6 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 178.9, 165.8, 163.6 (d, J = 249.9 Hz), 157.9, 146.5, 134.6 (d, J = 3.3 Hz), 131.1 (d, J = 8.4 Hz), 123.2, 115.6 (d, J = 21.6 Hz), 112.2, 72.5, 42.7, 33.2, 32.6, 23.1, 21.5, 20.4
¹⁹F NMR (377 MHz, CDCl₃)	δ -111.34
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₉H₂₅FN₃O₃S 394.1595; Found 394.1590

tert-Butyl 3-hydroxy-3-(prop-1-en-2-yl)azetidine-1-carboxylate
¹H NMR (400 MHz, CDCl₃)	δ 5.06 (t, J = 0.9 Hz, 1H), 4.96 (p, J = 1.4 Hz, 1H), 4.09 (d, J = 9.2 Hz, 2H), 3.87 (dd, J = 9.3, 1.0 Hz, 2H), 2.90 (d, J = 3.6 Hz, 1H), 1.83 (dd, J = 1.5, 0.8 Hz, 3H), 1.42 (s, 9H)
¹³C NMR (101 MHz, CDCl₃)	δ 156.6, 145.1, 111.7, 79.9, 72.6, 28.5, 18.0
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₁H₁₉NNaO₃ 236.1257; Found 236.1255

(1R,2S,5R)-2-(3-Hydroxyprop-1-en-2-yl)-5-methylcyclohexan-1-ol
¹H NMR (400 MHz, CDCl₃)	δ 5.10 (q, J = 1.4 Hz, 1H), 5.00 – 4.92 (m, 1H), 4.09 – 4.02 (m, 2H), 3.72 (t, J = 6.0 Hz, 2H), 3.15 (s, 2H), 2.35 (td, J = 6.0, 1.1 Hz, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 146.3, 113.7, 66.2, 61.8, 37.1
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₅H₁₀NaO₂ 125.0573; Found 125.0573

(1R,2S,5R)-2-(3-Hydroxyprop-1-en-2-yl)-5-methylcyclohexan-1-ol
¹H NMR (400 MHz, CDCl₃)	δ 5.19 (q, J = 1.3 Hz, 1H), 5.04 (dd, J = 1.3, 0.7 Hz, 1H), 4.18 – 4.01 (m, 2H), 3.53 (ddd, J = 10.9, 10.0, 4.2 Hz, 1H), 2.50 (s, 2H), 2.01 (dtd, J = 12.3, 3.9, 1.8 Hz, 1H), 1.94 (ddd, J = 13.3, 10.0, 3.5 Hz, 1H), 1.78 – 1.62 (m, 2H), 1.59 – 1.45 (m, 1H), 1.41 – 1.28 (m, 1H), 1.08 – 0.97 (m, 1H), 0.96 – 0.86 (m, 4H)
¹³C NMR (101 MHz, CDCl₃)	δ 150.9, 112.7, 73.4, 65.8, 50.2, 43.7, 34.6, 31.7, 31.4, 22.3
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₀H₁₈NaO₂ 193.1199; Found 193.1199
Optical rotation	[α]28.9_D = -41.8 (c = 1.08, CHCl3)

4-Methyl-1-tosyl-2,5-dihydro-1H-imidazole
¹H NMR (400 MHz, CDCl₃)	δ 7.72 – 7.65 (m, 2H), 7.35 – 7.28 (m, 2H), 5.16 (dp, J = 5.8, 1.9 Hz, 2H), 4.04 – 3.95 (m, 2H), 2.41 (s, 3H), 1.93 (t, J = 2.0 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.1, 144.2, 133.7, 130.1, 127.5, 78.5, 57.7, 21.6, 17.7
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₁H₁₅N₂O₂S₂ 239.0849; Found 239.0848
IR (FT-IR, 64 scans, cm⁻¹)	v = 2924, 2864, 1662, 1595, 1450, 1387, 1337, 1229, 1157, 1092, 1028, 847, 814, 710, 671, 584, 546

tert-Butyl 4-Methyl-2,5-dihydro-1H-imidazole-1-carboxylate
¹H NMR (500 MHz, DMSO, 25 °C)	δ 5.00 (dp, J = 5.9, 1.9 Hz, 2H), 4.04 (s, 2H), 1.97 (d, J = 2.7 Hz, 3H), 1.40 (s, 9H)
¹H NMR (500 MHz, DMSO, 80 °C)	δ 5.08 – 4.95 (m, 2H), 4.05 (ddt, J = 4.5, 3.4, 0.7 Hz, 2H), 1.98 (tt, J = 1.9, 0.7 Hz, 3H), 1.43 (s, 9H)
¹³C NMR (126 MHz, DMSO, 25 °C)	δ 169.8, 152.2, 79.1, 75.8, 55.8, 28.1, 17.4
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₇H₂₇N₆O₂ 347.2190; Found 347.2190
IR (FT-IR, 64 scans, cm⁻¹)	v = 2976, 2877, 1753, 1697, 1657, 1479, 1391, 1365, 1338, 1248, 1165, 1113, 1055, 1011, 891, 770, 546, 463

2a′
¹H NMR (500 MHz, MeOD)	δ 3.63 – 3.54 (m, 2H), 3.48 (d, J = 12.0 Hz, 1H), 3.24 (d, J = 8.8 Hz, 1H), 1.39 (s, 3H)
¹³C NMR (126 MHz, MeOD)	δ 162.8, 84.4, 67.3, 48.8, 22.8
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₅H₉NNaO₃ 154.0475; Found 154.0475

tert-Butyl 4-(4-(4-methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidin-2-yl)piperazine-1-carboxylate
¹H NMR (500 MHz, d₆-DMSO, 80 °C)	δ 7.43 – 7.28 (m, 5H), 5.16 – 5.09 (m, 4H), 4.20 – 4.04 (m, 2H), 2.00 (tt, J = 1.9, 0.7 Hz, 3H)
¹³C NMR (126 MHz, d₆-DMSO, 80 °C)	δ 169.0, 152.3, 136.5, 127.9, 127.4, 127.1, 75.6, 65.7, 55.5, 16.8
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₂H₁₅N₂O₂ 219.1128; Found 219.1128
IR (FT-IR, 64 scans, cm⁻¹)	v = 2924, 2879, 1701, 1657, 1499, 1448, 1414, 1360, 1331, 1244, 1196, 1109, 1053, 964, 914, 766, 696, 600, 550

(9H-Fluoren-9-yl)methyl 4-methyl-2,5-dihydro-1H-imidazole-1-carboxylate
¹H NMR (400 MHz, CDCl₃)	δ 7.77 (d, J = 7.7 Hz, 2H), 7.59 (dq, J = 7.4, 0.9 Hz, 2H), 7.44 – 7.36 (m, 2H), 7.32 (td, J = 7.4, 1.2 Hz, 2H), 5.23 (t, J = 10.5 Hz, 2H), 4.43 (t, J = 5.7 Hz, 2H), 4.31 – 4.12 (m, 3H), 2.10 (t, J = 1.9 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.9, 169.5, 153.4, 144.0, 141.5, 127.9, 127.2, 125.1, 120.2, 77.0, 76.3, 67.6, 67.4, 56.6, 56.0, 47.4, 18.1
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₉H₁₉N₂O₂ 307.1441; Found 307.1439
IR (FT-IR, 64 scans, cm⁻¹)	v = 2872, 1703, 1653, 1448, 1416, 1360, 1329, 1242, 1188, 1113, 1055, 976, 893, 737, 594, 538, 426

1-Tosyl-2,5-dihydro-1H-imidazole
¹H NMR (500 MHz, CDCl₃)	δ 7.74 – 7.68 (m, 2H), 7.40 (tt, J = 2.6, 0.9 Hz, 1H), 7.35 – 7.31 (m, 2H), 5.26 (ddd, J = 4.5, 4.1, 2.6 Hz, 2H), 4.14 (ddd, J = 4.9, 4.1, 0.9 Hz, 2H), 2.42 (dq, J = 0.8, 0.4 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 160.8, 144.4, 133.7, 130.2, 127.6, 78.8, 56.7, 21.7
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₀H₁₃N₂O₂S 225.0692; Found 225.0690
IR (FT-IR, 64 scans, cm⁻¹)	v = 2951, 2881, 1599, 1454, 1340, 1306, 1155, 1087, 1040, 970, 920, 814, 708, 663, 598, 546

4-(((tert-Butyldimethylsilyl)oxy)methyl)-1-tosyl-2,5-dihydro-1H-imidazole
¹H NMR (400 MHz, CDCl₃)	δ 7.71 (d, J = 7.9 Hz, 2H), 7.32 (d, J = 7.9 Hz, 2H), 5.25 (s, 2H), 4.27 (s, 2H), 4.20 (d, J = 4.3 Hz, 2H), 2.43 (t, J = 2.6 Hz, 3H), 0.86 (dt, J = 3.0, 1.4 Hz, 9H), 0.02 (t, J = 2.8 Hz, 6H)
¹³C NMR (101 MHz, CDCl₃)	δ 173.1, 144.3, 133.8, 130.1, 127.6, 78.9, 62.3, 55.5, 25.8, 21.7, 18.3, -5.5
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₇H₂₈N₂NaO₃SSi 391.1482; Found 391.1479
IR (FT-IR, 64 scans, cm⁻¹)	v = 2929, 1664, 1597, 1462, 1410, 1350, 1254, 1161, 1090, 1007, 835, 777, 708, 665, 594, 548

tert-Butyl 2,5-dihydro-1H-imidazole-1-carboxylate
¹H NMR (400 MHz, CDCl₃)	δ 7.60 (s, 1H), 5.39 – 5.02 (m, 2H), 4.19 (s, 2H), 1.46 (s, 9H)
¹³C NMR (101 MHz, CDCl₃)	δ 161.8, 153.1, 80.4, 76.5, 54.9, 28.5
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₈H₁₄N₂NaO₂ 193.0947; Found 193.0945
IR (FT-IR, 64 scans, cm⁻¹)	v = 2978, 1689, 1477, 1392, 1311, 1246, 1149, 1119, 910, 881, 770, 727, 646, 552

tert-Butyl 4-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dihydro-1H-imidazole-1-carboxylate
¹H NMR (400 MHz, CDCl₃)	δ 5.36 – 5.08 (m, 2H), 4.41 (s, 2H), 4.35 – 4.11 (m, 2H), 1.47 (s, 9H), 0.90 (s, 9H), 0.08 (s, 6H)
¹³C NMR (101 MHz, CDCl₃)	δ 173.8, 153.2, 80.3, 76.6, 62.7, 53.8, 28.6, 25.9, 18.4, -5.4
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₅H₃₁N₂O₃Si 315.2098; Found 315.2095
IR (FT-IR, 64 scans, cm⁻¹)	v = 2929, 2858, 1703, 1659, 1473, 1391, 1342, 1254, 1161, 1101, 1007, 835, 775, 665, 548

Benzyl 2,5-Dihydro-1H-imidazole-1-carboxylate
¹H NMR (500 MHz, CDCl₃)	δ 7.65 (d, J = 17.9 Hz, 1H), 7.41 – 7.33 (m, 5H), 5.40 – 5.28 (m, 2H), 5.19 (s, 2H), 4.36 – 4.21 (m, 2H)
¹³C NMR (126 MHz, CDCl₃)	δ 161.7, 136.5, 128.7, 128.4, 128.2, 76.4, 67.4, 55.4, 54.9
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₁H₁₂N₂NaO₂ 227.0791; Found 227.0794
IR (FT-IR, 64 scans, cm⁻¹)	v = 3032, 2953, 2889, 1697, 1630, 1497, 1446, 1416, 1354, 1331, 1200, 1234, 1107, 1028, 955, 916, 885, 852, 764, 733, 696, 606, 555, 459

4-Methyl-1-tosyl-2,5-dihydro-1H-imidazole-3-¹⁵N
¹H NMR (600 MHz, CDCl₃)	δ 7.75 – 7.67 (m, 2H), 7.32 (d, J = 8.0 Hz, 2H), 5.17 (tq, J = 3.8, 1.9 Hz, 2H), 4.02 (q, J = 3.6 Hz, 2H), 2.42 (s, 3H), 1.94 (q, J = 2.2 Hz, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 169.4 (d, J = 4.7 Hz), 144.3, 133.7, 130.1, 127.6, 78.4 (d, J = 4.6 Hz), 57.7 (d, J = 2.6 Hz), 21.7, 17.7 (d, J = 7.7 Hz)
¹⁵N NMR (61 MHz, CDCl₃)	δ 302.79
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₁H₁₅NO₂S¹⁵N 240.0819; Found 240.0817
IR (FT-IR, 64 scans, cm⁻¹)	v = 1643, 1595, 1437, 1385, 1333, 1290, 1229, 1161, 1099, 1036, 866, 818, 710, 671, 588, 544, 492

N-(4-((4-Methyl-2,5-dihydro-1H-imidazol-1-yl)sulfonyl)phenyl)acetamide
¹H NMR (400 MHz, DMSO)	δ 10.36 (s, 1H), 7.90 – 7.62 (m, 4H), 5.02 (tq, J = 3.9, 1.8 Hz, 2H), 4.04 (t, J = 3.5 Hz, 2H), 2.09 (s, 3H), 1.83 (d, J = 1.9 Hz, 3H)
¹³C NMR (101 MHz, DMSO)	δ 169.4, 169.1, 143.7, 129.2, 128.7, 118.7, 77.90, 57.4, 24.2, 17.1
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₂H₁₆N₃O₃S 282.0907; Found 282.0908
IR (FT-IR, 64 scans, cm⁻¹)	v = 3336, 1701, 1661, 1589, 1529, 1375, 1325, 1261, 1229, 1149, 1090, 1022, 827, 723, 667, 619, 582, 548

1-(4-((4-Methyl-2,5-dihydro-1H-imidazol-1-yl)sulfonyl)phenyl)-5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazole
¹H NMR (400 MHz, CDCl₃)	δ 7.86 – 7.81 (m, 2H), 7.55 – 7.51 (m, 2H), 7.23 – 7.19 (m, 2H), 7.14 – 7.11 (m, 2H), 6.77 (s, 1H), 5.21 (tq, J = 3.9, 1.9 Hz, 2H), 4.07 – 4.00 (m, 2H), 2.41 (s, 3H), 2.00 (t, J = 1.9 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 168.8, 145.3, 144.3 (q, J = 38.5 Hz), 143.0, 139.9, 136.2, 129.8, 128.7, 128.4, 125.8, 125.6, 125.3 – 116.4 (m, apparent q), 106.4 (d, J = 2.2 Hz, apparent q), 78.5, 57.5, 21.4, 17.7
¹⁹F NMR (377 MHz, CDCl₃)	δ -62.50
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₂₁H₂₀F₃N₄O₂S 449.1254; Found 449.1254
IR (FT-IR, 64 scans, cm⁻¹)	v = 2980, 2887, 1661, 1595, 1473, 1373, 1337, 1273, 1232, 1159, 1128, 1097, 1043, 976, 847, 802, 762, 721, 669, 633, 577, 513, 478

3-(4-Chloro-3-((4-methyl-2,5-dihydro-1H-imidazol-1-yl)sulfonyl)phenyl)-3-hydroxy-isoindolin-1-one
¹H NMR (500 MHz, d₆-DMSO)	δ 9.39 (s, 1H), 8.09 (d, J = 2.2 Hz, 1H), 7.72 – 7.66 (m, 2H), 7.64 (dd, J = 8.4, 2.2 Hz, 1H), 7.58 (td, J = 7.5, 1.3 Hz, 1H), 7.53 (td, J = 7.4, 1.1 Hz, 1H), 7.35 (dt, J = 7.5, 1.0 Hz, 1H), 7.29 (s, 1H), 5.22 (tp, J = 4.2, 2.1 Hz, 2H), 4.15 (q, J = 3.1 Hz, 2H), 1.96 (t, J = 1.9 Hz, 3H)
¹³C NMR (126 MHz, d₆-DMSO)	δ 169.3, 168.3, 149.7, 142.4, 135.8, 132.8, 132.6, 131.8, 130.5, 130.4, 129.5, 127.8, 122.9, 122.8, 86.5, 77.9, 57.1, 17.3
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₈H₁₇ClN₃O₄S 406.0623; Found 406.0624
IR (FT-IR, 64 scans, cm⁻¹)	v = 3142, 3074, 2852, 1702, 1668, 1607, 1327, 1190, 1149, 1112, 1057, 957, 833, 768, 725, 687, 608, 575, 536, 503

5-Chloro-2-methoxy-N-(4-((4-methyl-2,5-dihydro-1H-imidazol-1-yl)sulfonyl)phenethyl)-benzamide
¹H NMR (400 MHz, CDCl₃)	δ 8.16 (d, J = 2.8 Hz, 1H), 7.84 – 7.75 (m, 3H), 7.45 – 7.40 (m, 2H), 7.38 (dd, J = 8.8, 2.8 Hz, 1H), 6.88 (d, J = 8.8 Hz, 1H), 5.20 (tq, J = 3.8, 1.9 Hz, 2H), 4.05 (t, J = 3.8 Hz, 2H), 3.80 (s, 3H), 3.74 (td, J = 6.8, 5.7 Hz, 2H), 3.02 (t, J = 6.9 Hz, 2H), 1.97 (t, J = 1.9 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.2, 164.2, 156.0, 145.5, 135.2, 132.6, 132.1, 130.1, 127.8, 127.0, 122.8, 113.0, 78.6, 57.7, 56.4, 40.8, 35.7, 17.8
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₂₀H₂₃ClN₃O₄S 436.1092; Found 436.1092
IR (FT-IR, 64 scans, cm⁻¹)	v = 3383, 2931, 2847, 1645, 1594, 1529, 1479, 1456, 1344, 1271, 1240, 1159, 1124, 1013, 833, 708, 679, 646, 592, 565, 546

5-Methyl-4-(4-((4-methyl-2,5-dihydro-1H-imidazol-1-yl)sulfonyl)phenyl)-3-phenyl-isoxazole
¹H NMR (400 MHz, CDCl₃)	δ 7.91 – 7.78 (m, 2H), 7.45 – 7.33 (m, 7H), 5.25 (tq, J = 3.9, 1.9 Hz, 2H), 4.11 (t, J = 3.8 Hz, 2H), 2.52 (s, 3H), 2.01 (t, J = 1.9 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.2, 167.4, 161.2, 136.3, 135.9, 130.6, 129.9, 128.9, 128.6, 128.5, 127.9, 114.5, 78.5, 57.8, 17.8, 12.0
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₂₀H₂₀N₃O₃S 382.122; Found 382.1218
IR (FT-IR, 64 scans, cm⁻¹)	v = 2883, 1661, 1626, 1593, 1439, 1340, 1242, 1165, 1092, 1028, 976, 916, 858, 750, 696, 625, 517, 449

N,N-Dimethyl-2-((4-methyl-2,5-dihydro-1H-imidazol-1-yl)sulfonyl)nicotinamide
¹H NMR (400 MHz, CDCl₃)	δ 8.67 (dd, J = 4.7, 1.7 Hz, 1H), 7.73 (dd, J = 7.8, 1.7 Hz, 1H), 7.53 (dd, J = 7.8, 4.7 Hz, 1H), 5.64 – 5.32 (m, 2H), 4.34 (t, J = 3.9 Hz, 2H), 3.12 (s, 3H), 2.85 (s, 3H), 1.99 (dq, J = 1.9, 1.1 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.2, 167.2, 152.2, 149.9, 136.7, 133.4, 126.9, 79.3, 58.3, 39.0, 35.1, 17.8
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₂H₁₆N₄NaO₃S 319.0835; Found 319.0834
IR (FT-IR, 64 scans, cm⁻¹)	v = 3007, 2931, 2879, 1634 (broad), 1580, 1506, 1437, 1392, 1346, 1275, 1211, 1167, 1115, 1036, 976, 916, 818, 764, 665, 633, 604, 569, 474

3-((4-Methyl-2,5-dihydro-1H-imidazol-1-yl)sulfonyl)-N-(m-tolyl)pyridin-4-amine
¹H NMR (400 MHz, MeOD)	δ 8.65 (s, 1H), 8.19 (d, J = 6.1 Hz, 1H), 7.35 (t, J = 7.7 Hz, 1H), 7.19 – 7.04 (m, 3H), 6.95 (dd, J = 6.2, 0.5 Hz, 1H), 5.27 (tq, J = 3.8, 1.9 Hz, 2H), 4.30 – 4.20 (m, 2H), 2.38 (d, J = 0.8 Hz, 3H), 2.02 (td, J = 1.9, 0.9 Hz, 3H)
¹³C NMR (101 MHz, MeOD)	δ 172.9, 153.9, 152.1, 151.5, 141.4, 138.8, 130.9, 128.5, 126.4, 122.9, 118.6, 110.2, 78.6, 58.2, 21.3, 17.4
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₆H₁₉N₄O₂S 331.1223; Found 331.1224
IR (FT-IR, 64 scans, cm⁻¹)	v = 3028, 2856, 2740, 2609, 1634, 1576, 1489, 1460, 1414, 1342, 1259, 1229, 1169, 1088, 1034, 957, 822, 770, 625, 573, 519, 476

4-Methyl-1-((2-(trifluoromethyl)benzyl)sulfonyl)-2,5-dihydro-1H-imidazole
¹H NMR (500 MHz, CDCl₃)	δ 7.81 (d, J = 7.8 Hz, 1H), 7.73 – 7.69 (m, 1H), 7.61 (tt, J = 7.9, 1.0 Hz, 1H), 7.50 (tt, J = 7.6, 1.1 Hz, 1H), 5.01 (dp, J = 6.0, 1.9 Hz, 2H), 4.49 (s, 2H), 4.02 – 3.93 (m, 2H), 2.01 (td, J = 1.9, 1.0 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 168.7, 133.3, 132.1 (q, J = 1.2 Hz), 129.5 (q, J = 30.1 Hz), 129.0, 127.27 (dd, J = 4.1, 2.5 Hz), 126.6 (q, J = 5.5 Hz), 124.0 (q, J = 273.9 Hz), 78.6, 58.8 – 57.0 (m), 54.4 (q, J = 2.3 Hz), 17.6
¹⁹F NMR (471 MHz, CDCl₃)	δ -58.27
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₂H₁₄F₃N₂O₂S 307.0723; Found 307.0722
IR (FT-IR, 64 scans, cm⁻¹)	v = 2872, 1662, 1607, 1448, 1335, 1313,1230, 1180, 1159, 1138, 1119, 1034, 870, 851, 831, 783, 756, 723, 673, 631, 554, 527, 498, 474

4-Methyl-1-(thiophen-2-ylsulfonyl)-2,5-dihydro-1H-imidazole
¹H NMR (500 MHz, CDCl₃)	δ 7.66 – 7.58 (m, 2H), 7.15 (dd, J = 5.0, 3.8 Hz, 1H), 5.21 (dp, J = 5.7, 1.9 Hz, 2H), 4.12 – 3.99 (m, 2H), 1.97 (t, J = 1.9 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 169.0, 136.3, 132.8, 132.7, 127.9, 78.7, 57.9, 17.8
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₈H₁₁N₂O₂S₂ 231.0256; Found 231.0257
IR (FT-IR, 64 scans, cm⁻¹)	v = 3113, 2835, 1661, 1458, 1398, 1348, 1229, 1134, 1155, 1095, 1076, 1013, 856, 739, 675, 602, 577, 555, 480

((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl 4-methyl-2,5-dihydro-1H-imidazole-1-sulfonate
¹H NMR (400 MHz, CDCl₃)	δ 5.30 (tq, J = 4.1, 1.9 Hz, 2H), 4.61 (dd, J = 7.9, 2.6 Hz, 1H), 4.30 (d, J = 2.6 Hz, 1H), 4.25 – 4.21 (m, 2H), 4.21 – 4.17 (m, 2H), 4.15 (d, J = 10.3 Hz, 1H), 3.90 (dd, J = 13.0, 1.9 Hz, 1H), 3.75 (dd, J = 13.0, 0.8 Hz, 1H), 2.09 (t, J = 2.0 Hz, 3H), 1.55 – 1.52 (m, 3H), 1.45 (s, 3H), 1.38 (s, 3H), 1.34 (s, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.1, 109.4, 109.3, 100.8, 79.6, 70.7, 70.3, 70.3, 70.0, 61.5, 58.3, 26.6, 25.9, 25.3, 24.1, 17.8
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₆H₂₇N₂O₈S 407.1483; Found 407.1482
Optical rotation	[α]29.5_D = -40.2 (c = 1.33, MeOH)
IR (FT-IR, 64 scans, cm⁻¹)	v = 2989, 2937, 1736, 1662, 1454, 1371, 1250, 1203, 1178, 1101, 1068, 993, 912, 885, 865, 800, 756, 712, 671, 608, 554, 521

8-((4-Methyl-2,5-dihydro-1H-imidazol-1-yl)sulfonyl)quinoline
¹H NMR (400 MHz, CDCl₃)	δ 9.03 (dd, J = 4.2, 1.8 Hz, 1H), 8.54 (dd, J = 7.4, 1.5 Hz, 1H), 8.25 (dd, J = 8.4, 1.8 Hz, 1H), 8.06 (dd, J = 8.2, 1.5 Hz, 1H), 7.65 (dd, J = 8.2, 7.4 Hz, 1H), 7.53 (dd, J = 8.3, 4.2 Hz, 1H), 5.49 (tq, J = 3.8, 1.9 Hz, 2H), 4.60 – 4.49 (m, 2H), 1.97 (t, J = 1.9 Hz, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 169.4, 151.3, 144.1, 136.8, 136.7, 134.1, 133.9, 129.2, 125.7, 122.3, 78.8, 58.5, 17.8
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₃H₁₃N₃NaO₂S 298.0621; Found 298.0620
IR (FT-IR, 64 scans, cm⁻¹)	v = 2899, 1657, 1493, 1325, 1211, 1167, 1140, 1097, 1041, 833, 787, 679, 608, 581, 552, 523, 484

2-(4-Methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidine
¹H NMR (400 MHz, CDCl₃)	δ 8.32 (d, J = 4.8 Hz, 2H), 6.54 (t, J = 4.8 Hz, 1H), 5.40 (tq, J = 3.9, 1.9 Hz, 2H), 4.32 (t, J = 4.0 Hz, 2H), 2.13 (t, J = 2.0 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 170.3, 158.8, 158.1, 110.4, 77.2, 56.9, 18.2
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₈H₁₁N₄ 163.0978; Found 163.0979
IR (FT-IR, 64 scans, cm⁻¹)	v = 3356, 2924, 1730, 1691, 1657, 1581, 1551, 1510, 1448, 1419, 1383, 1333, 1290, 1229, 1180, 1065, 797, 634, 505

2,4-Dichloro-6-(4-methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidine
¹H NMR (500 MHz, CDCl₃)	δ 6.19 (s, 1H), 5.60 – 5.13 (m, 2H), 4.53 – 4.00 (m, 2H), 2.17 (d, J = 2.1 Hz, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 170.9, 168.1, 160.2, 159.9, 159.8, 100.9, 100.6, 77.8, 76.4, 57.3, 56.0, 18.2
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₈H₉Cl₂N₄ 231.0199; Found 231.0197
IR (FT-IR, 64 scans, cm⁻¹)	v = 3113, 2922, 2858, 1734, 1661, 1572, 1487, 1379, 1281, 1209, 1157, 1047, 964, 908, 827, 729, 669, 615, 555, 447

2-Chloro-4-methyl-6-(4-methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidine
¹H NMR (500 MHz, d₆-DMSO, 25 °C)	δ 6.37 (s, 1H), 5.22 (s, 2H), 4.22 (s, 2H), 2.25 (d, J = 0.7 Hz, 3H), 2.06 (t, J = 1.9 Hz, 3H)
¹H NMR (500 MHz, d₆-DMSO, 80 °C)	δ 6.34 (q, J = 0.7 Hz, 1H), 5.24 (dp, J = 5.5, 1.9 Hz, 2H), 4.30 – 4.19 (m, 2H), 2.28 (d, J = 0.7 Hz, 3H), 2.08 (tt, J = 1.9, 0.7 Hz, 3H)
¹³C NMR (126 MHz, d₆-DMSO)	δ 170.1, 169.1, 166.9, 159.5, 159.0, 101.5, 101.2, 76.4, 76.1, 56.3, 55.8, 23.1, 17.5
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₉H₁₂ClN₄ 211.0745; Found 211.0744
IR (FT-IR, 64 scans, cm⁻¹)	v = 2922, 1657, 1597, 1554, 1504, 1429, 1367, 1283, 1211, 1148, 1055, 966, 914, 881, 827, 758, 687, 577, 544

Methyl 2-Chloro-6-(4-methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidine-4-carboxylate
¹H NMR (500 MHz, CDCl₃)	δ 7.01 – 6.83 (m, 1H), 5.56 – 5.23 (m, 2H), 4.52 – 4.15 (m, 2H), 3.96 (s, 3H), 2.17 (s, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 170.8, 168.2, 164.3, 161.5, 160.3, 160.1, 155.4, 155.3, 103.5, 103.1, 77.8, 76.6, 57.3, 56.2, 53.5, 18.2, 18.1
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₀H₁₂ClN₄O₂ 255.0643; Found 255.0641
IR (FT-IR, 64 scans, cm⁻¹)	v = 2954, 2860, 1730, 1661, 1591, 1531, 1502, 1439, 1387, 1340, 1290, 1248, 1211, 1157, 1047, 966, 912, 860, 771, 723, 644

(2-((5-Chloro-2-(4-methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide
¹H NMR (500 MHz, CDCl₃)	δ 10.96 (s, 1H), 8.78 (ddd, J = 8.6, 4.4, 1.0 Hz, 1H), 8.03 (s, 1H), 7.52 (ddt, J = 8.6, 7.2, 1.4 Hz, 1H), 7.29 – 7.23 (m, 1H), 7.10 (tdd, J = 7.5, 2.3, 1.1 Hz, 1H), 5.40 (dq, J = 4.0, 2.0 Hz, 2H), 4.32 (t, J = 4.0 Hz, 2H), 2.20 – 2.11 (m, 3H), 1.83 (d, J = 13.1 Hz, 6H)
¹³C NMR (126 MHz, CDCl₃)	δ 170.4, 156.6, 156.0, 154.8, 132.5 (d, J = 2.2 Hz), 129.8 (d, J = 11.0 Hz), 122.2, 122.1 (d, J = 7.1 Hz), 119.7 (d, J = 95.5 Hz), 105.5, 77.4, 57.1, 18.8 (d, J = 71.6 Hz), 18.3
³¹P NMR (162 MHz, CDCl₃)	δ 44.18
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₆H₂₀ClN₅OP 364.1089; Found 364.1087
IR (FT-IR, 64 scans, cm⁻¹)	v = 1655, 1614, 1524, 1441, 1385, 1310, 1246, 1140, 941, 874, 752, 501, 430

5-Chloro-N-(2-(isopropylsulfonyl)phenyl)-2-(4-methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidin-4-amine
¹H NMR (400 MHz, CDCl₃)	δ 9.64 (s, 1H), 8.73 (dd, J = 8.5, 1.1 Hz, 1H), 8.09 (s, 1H), 7.90 (dd, J = 8.0, 1.6 Hz, 1H), 7.67 – 7.61 (m, 1H), 7.23 (ddd, J = 8.3, 7.4, 1.1 Hz, 1H), 5.40 (td, J = 3.9, 2.0 Hz, 2H), 4.33 (t, J = 4.0 Hz, 2H), 3.24 (hept, J = 6.8 Hz, 1H), 2.16 (t, J = 1.9 Hz, 3H), 1.31 (d, J = 6.9 Hz, 6H)
¹³C NMR (151 MHz, CDCl₃)	δ 170.5, 156.6, 155.4, 155.3, 139.0, 134.6, 131.4, 124.2, 122.9, 122.8, 105.1, 77.4, 57.1, 55.8, 18.2, 15.5
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₇H₂₁ClN₅O₂S 394.1099; Found 394.1099
IR (FT-IR, 64 scans, cm⁻¹)	v = 3296, 2933, 2860, 1659, 1603, 1556, 1504, 1439, 1315, 1257, 1126, 1051, 949, 878, 771, 687, 586, 519, 465

4-Fluoro-6-(5-fluoro-2-(4-methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidin-4-yl)-1-isopropyl-2-methyl-1H-benzo[d]imidazole
¹H NMR (500 MHz, CDCl₃)	δ 8.26 (d, J = 4.1 Hz, 1H), 8.10 (d, J = 1.3 Hz, 1H), 7.78 (dd, J = 11.7, 1.3 Hz, 1H), 5.47 (td, J = 4.1, 2.1 Hz, 2H), 4.69 (h, J = 7.0 Hz, 1H), 4.40 (t, J = 4.0 Hz, 2H), 2.66 (s, 3H), 2.16 (t, J = 1.9 Hz, 3H), 1.67 (d, J = 7.0 Hz, 6H)
¹³C NMR (151 MHz, CDCl₃)	δ 170.5, 155.7 (d, J = 2.3 Hz), 154.2, 153.5, 152.6, 151.2, 147.1 (d, J = 26.9 Hz), 136.5 (d, J = 9.2 Hz), 134.0 (d, J = 17.2 Hz), 128.0, 108.8 (dd, J = 10.6, 3.4 Hz), 108.0 (dd, J = 20.0, 5.6 Hz), 77.6, 57.4, 48.7, 21.6, 18.2, 15.2
¹⁹F NMR (470 MHz, CDCl₃)	δ -128.38 (d, J = 11.6 Hz), -153.12 – -154.34 (m)
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₉H₂₁F₂N₆ 371.1790; Found 371.1789
IR (FT-IR, 64 scans, cm⁻¹)	v = 2995, 2862, 1653, 1585, 1510, 1416, 1327, 1259, 1200, 1146, 1045, 932, 852, 777, 708, 640, 575, 509

N-(tert-Butyl)-3-((5-methyl-2-(4-methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidin-4-yl)amino)benzenesulfonamide
¹H NMR (500 MHz, d₆-DMSO)	δ 8.68 (s, 1H), 8.51 (s, 1H), 7.98 – 7.74 (m, 2H), 7.62 – 7.35 (m, 3H), 5.23 (s, 2H), 4.26 (s, 2H), 2.09 (d, J = 0.8 Hz, 3H), 2.04 (d, J = 1.9 Hz, 3H), 1.12 (s, 9H)
¹³C NMR (126 MHz, d₆-DMSO)	δ 170.1, 158.7, 157.2, 156.4, 144.3, 140.6, 128.8, 123.3, 119.7, 118.3, 104.1, 76.6, 53.2, 29.8, 17.6, 13.4
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₉H₂₇N₆O₂S 403.1911; Found 403.1910
IR (FT-IR, 64 scans, cm⁻¹)	v = 2968, 2868, 1659, 1610, 1545, 1462, 1387, 1306, 1240, 1159, 1097, 999, 939, 797, 689, 586, 494

tert-Butyl 4-(4-(4-methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidin-2-yl)piperazine-1-carboxylate
¹H NMR (400 MHz, CDCl₃)	δ 7.95 (d, J = 5.9 Hz, 1H), 5.64 (d, J = 5.9 Hz, 1H), 5.31 (s, 2H), 4.23 (s, 2H), 3.85 – 3.71 (m, 4H), 3.51 – 3.45 (m, 4H), 2.16 (t, J = 1.9 Hz, 3H), 1.48 (s, 9H)
¹³C NMR (126 MHz, CDCl₃)	δ 161.5, 159.0, 156.3, 155.0, 93.9, 80.0, 76.6, 56.3, 43.7 (2 C), 28.6, 18.2
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₇H₂₇N₆O₂ 347.2190; Found 347.2190
IR (FT-IR, 64 scans, cm⁻¹)	v = 2974, 2854, 1698, 1661, 1556, 1416, 1365, 1234, 1163, 997, 864, 789, 685, 536, 449

N,2,3-Trimethyl-N-(2-(4-methyl-2,5-dihydro-1H-imidazol-1-yl)pyrimidin-4-yl)-2H-indazol-6-amine
¹H NMR (600 MHz, CDCl₃)	δ 7.72 (d, J = 5.9 Hz, 1H), 7.55 (d, J = 8.7 Hz, 1H), 7.43 (s, 1H), 6.84 (d, J = 8.7 Hz, 1H), 5.68 (d, J = 6.1 Hz, 1H), 5.40 (s, 2H), 4.33 (d, J = 4.0 Hz, 2H), 4.07 (s, 3H), 3.47 (s, 3H), 2.59 (s, 3H), 2.11 (s, 3H)
¹³C NMR (151 MHz, CDCl₃)	δ 170.5, 162.8, 158.8, 155.5, 148.0, 142.8, 132.0, 121.2, 120.6, 119.9, 114.5, 95.6, 77.1, 56.8, 37.6, 37.5, 18.2, 10.0
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₈H₂₂N₇ 336.1931; Found 336.1930
IR (FT-IR, 64 scans, cm⁻¹)	v = 2856, 1655, 1587, 1556, 1514, 1456, 1373, 1309, 1250, 1140, 1107, 1067, 1036, 968, 914, 831, 789, 683, 492

4-Methyl-2,5-dihydrooxazole
¹H NMR (400 MHz, CD₃CN)	δ 5.39 (tq, J = 4.6, 1.9 Hz, 2H), 4.51 – 4.47 (m, 2H), 2.04 (tt, J = 1.9, 0.7 Hz, 3H)

5,5-Dimethyl-2,5-dihydrooxazole
¹H NMR (400 MHz, CD₃CN)	δ 7.45 (t, J = 2.7 Hz, 1H), 5.42 (d, J = 2.7 Hz, 2H), 1.29 (s, 6H)

1-Oxa-3-azaspiro[4.5]dec-3-ene
¹H NMR (500 MHz, CDCl₃)	δ 7.42 (t, J = 2.7 Hz, 1H), 5.51 (d, J = 2.7 Hz, 2H), 1.73 – 1.56 (m, 9H), 1.44 – 1.34 (m, 1H)
¹³C NMR (126 MHz, CDCl₃)	δ 166.7, 94.5, 89.6, 33.5, 25.3, 22.9
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₈H₁₄NO 140.1070; Found 140.1068
IR (FT-IR, 64 scans, cm⁻¹)	v = 2931, 2858, 1742, 1632, 1448, 1188, 1155, 1080, 1041, 937, 854, 733, 689, 656, 467

4-(((tert-Butyldimethylsilyl)oxy)methyl)-2,5-dihydrooxazole
¹H NMR (500 MHz, CDCl₃)	δ 5.56 (tt, J = 4.9, 2.0 Hz, 2H), 4.65 (tt, J = 4.7, 0.8 Hz, 2H), 4.51 (tt, J = 1.9, 0.8 Hz, 2H), 0.90 (s, 9H), 0.09 (s, 6H)
¹³C NMR (126 MHz, CDCl₃)	δ 173.2, 97.0, 74.3, 61.8, 25.9, 18.4, -5.4
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₀H₂₁NNaO₂Si 238.1234; Found 238.1230
IR (FT-IR, 64 scans, cm⁻¹)	v = 2929, 2858, 1666, 1464, 1362, 1254, 1103, 1007, 916, 833, 775, 669

4-Phenyl-2,5-dihydrooxazole
¹H NMR (500 MHz, CDCl₃)	δ 7.81 – 7.70 (m, 1H), 7.54 – 7.41 (m, 1H), 5.82 – 5.74 (m, 1H), 4.98 (dd, J = 5.2, 4.4 Hz, 1H)
¹³C NMR (126 MHz, CDCl₃)	δ 167.8, 131.6, 131.0, 128.9, 127.8, 97.3, 73.4
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₄H₇NNaO₂ 124.0369; Found 124.0370
IR (FT-IR, 64 scans, cm⁻¹)	v = 2860, 1732, 1688, 1634, 1578, 1450, 1352, 1277, 1159, 1067, 1038, 912, 864, 760, 729, 690, 646, 563

4-(2,4-Difluorophenyl)-2,5-dihydrooxazole
¹H NMR (500 MHz, CDCl₃)	δ 8.12 (td, J = 8.5, 6.5 Hz, 1H), 7.04 – 6.94 (m, 1H), 6.87 (ddd, J = 11.1, 8.6, 2.5 Hz, 1H), 5.72 – 5.65 (m, 2H), 4.94 (td, J = 5.0, 3.1 Hz, 2H)
¹³C NMR (126 MHz, CDCl₃)	δ 165.1 (dd, J = 255.2, 12.3 Hz), 163.7 (dd, J = 3.8, 1.4 Hz), 162.2 (dd, J = 255.5, 12.2 Hz), 131.5 (dd, J = 10.1, 5.3 Hz), 115.6 (dd, J = 13.0, 3.8 Hz), 112.7 (dd, J = 21.7, 3.3 Hz), 105.7 – 103.2 (m), 95.6, 75.0 (d, J = 12.8 Hz)
¹⁹F NMR (471 MHz, CDCl₃)	δ -104.20 (d, J = 9.6 Hz), -109.41 (d, J = 9.6 Hz)
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₉H₈F₂NO 184.0568; Found 184.0568
IR (FT-IR, 64 scans, cm⁻¹)	v = 3051, 2879, 1737, 1614, 1587, 1504, 1427, 1350, 1263, 1221, 1142, 1105, 1041, 1003, 966, 910, 872, 818, 771, 735, 606, 567, 513, 457

(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-(2-((R)-5-methyl-2,5-dihydrooxazol-5-yl)ethyl)decahydronaphthalen-2-ol
¹H NMR (400 MHz, CDCl₃)	δ 7.34 (t, J = 2.7 Hz, 1H), 5.54 (d, J = 2.7 Hz, 2H), 1.88 – 1.70 (m, 3H), 1.67 – 1.61 (m, 2H), 1.61 – 1.55 (m, 2H), 1.45 – 1.32 (m, 4H), 1.29 (s, 3H), 1.27 – 1.15 (m, 2H), 1.14 – 1.08 (m, 4H), 1.03 (t, J = 4.1 Hz, 1H), 0.95 – 0.85 (m, 6H), 0.78 – 0.76 (m, 6H)
¹³C NMR (101 MHz, CDCl₃)	δ 167.1, 95.6, 90.8, 74.4, 62.0, 56.3, 44.9, 42.1, 41.6, 39.9, 39.4, 33.6, 33.4, 24.2, 23.1, 21.6, 20.7, 19.5, 18.6, 15.5
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₂₀H₃₅NNaO₂ 344.2560; Found 344.2558
IR (FT-IR, 64 scans, cm⁻¹)	v = 3338, 2924, 2847, 1635, 1450, 1365, 1188, 1132, 1178, 1038, 957, 845, 660
Optical rotation	[α]23.1D = -31.1 (c = 1.00, CHCl3)

N-(4-(4-Fluorophenyl)-6-isopropyl-5-(4-methyl-2,5-dihydrooxazol-5-yl)pyrimidin-2-yl)-N-methylmethanesulfonamide
¹H NMR (400 MHz, CDCl₃)	δ 7.73 – 7.50 (m, 2H), 7.17 (t, J = 8.6 Hz, 2H), 5.67 (s, 1H), 5.60 (t, J = 5.4 Hz, 1H), 5.51 – 5.39 (m, 1H), 3.58 (s, 3H), 3.51 (s, 3H), 2.96 (s, 1H), 1.84 (s, 3H), 1.29 (dd, J = 13.3, 6.5 Hz, 6H)
¹³C NMR (101 MHz, CDCl₃)	δ 178.2, 169.8, 167.8, 163.6 (d, J = 250.2 Hz), 158.1, 134.1 (d, J = 3.4 Hz), 131.4 (d, J = 8.5 Hz), 117.8, 115.6 (d, J = 21.8 Hz), 94.7, 83.6, 42.5, 33.2, 31.8, 23.5, 21.3, 16.1
¹⁹F NMR (376 MHz, CDCl₃)	δ -110.95
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₉H₂₃FN₄NaO₃S 429.1367; Found 429.1365
IR (FT-IR, 64 scans, cm⁻¹)	v = 2966, 2870, 1662, 1605, 1543, 1510, 1439, 1379, 1338, 1227, 1153, 1067, 1011, 961, 845, 777, 731, 646, 594, 561, 509

tert-Butyl 8-methyl-5-oxa-2,7-diazaspiro[3.4]oct-7-ene-2-carboxylate
¹H NMR (500 MHz, CDCl₃)	δ 5.43 (q, J = 2.1 Hz, 2H), 4.21 – 3.96 (m, 4H), 2.23 (t, J = 2.1 Hz, 3H), 1.46 (s, 9H)
¹³C NMR (126 MHz, CDCl₃)	δ 169.4, 156.5, 94.9, 83.7, 80.4, 28.5, 13.9
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₁₁H₁₈N₂NaO₃ 249.1210; Found 249.1208
IR (FT-IR, 64 scans, cm⁻¹)	v = 2974, 2879, 1688, 1655, 1383, 1308, 1250, 1165, 1095, 1067, 995, 949, 851, 802, 771, 654, 584

2-(2,5-Dihydrooxazol-4-yl)ethan-1-ol
¹H NMR (500 MHz, MeOD)	δ 5.44 (tt, J = 4.7, 1.7 Hz, 2H), 4.60 – 4.52 (m, 2H), 3.83 (t, J = 6.3 Hz, 2H), 2.67 – 2.56 (m, 2H)
¹³C NMR (126 MHz, MeOD)	δ 174.5, 96.5, 76.3, 59.6, 34.1
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₅H₁₀NO₂ 116.0706; Found 116.0706
IR (FT-IR, 64 scans, cm⁻¹)	v = 3317, 2924, 2875, 1657, 1410, 1194, 1040, 916, 687, 471

(1R,2S,5R)-2-(2,5-Dihydrooxazol-4-yl)-5-methylcyclohexan-1-ol
¹H NMR (500 MHz, CDCl₃)	δ 5.59 – 5.46 (m, 2H), 4.61 (dddd, J = 14.0, 5.8, 3.6, 0.6 Hz, 1H), 4.48 (dddd, J = 13.9, 5.8, 3.7, 0.7 Hz, 1H), 3.91 (s, 1H), 3.83 (ddd, J = 11.2, 9.5, 4.3 Hz, 1H), 2.22 (tt, J = 10.9, 1.9 Hz, 1H), 2.04 (dddd, J = 12.6, 4.2, 3.4, 1.9 Hz, 1H), 1.88 (dq, J = 13.3, 3.6 Hz, 1H), 1.77 – 1.69 (m, 1H), 1.52 (dddd, J = 15.5, 9.1, 6.8, 3.5 Hz, 1H), 1.31 (qd, J = 13.1, 3.7 Hz, 1H), 1.07 (td, J = 12.3, 11.2 Hz, 1H), 1.03 – 0.94 (m, 4H)
¹³C NMR (126 MHz, CDCl₃)	δ 175.9, 96.3, 74.4, 71.6, 46.4, 42.3, 34.1, 31.1, 28.0, 22.2
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₅H₁₀NO₂ 116.0706; Found 116.0706
IR (FT-IR, 64 scans, cm⁻¹)	v = 3373, 2924, 1651, 1450, 1348, 1095, 1047, 1014, 905, 729, 646
Optical rotation	[α]28.9D = -27.4 (c = 3.99, CHCl3)

N-(2-aminopropyl)-N,4-dimethylbenzenesulfonamide
¹H NMR (500 MHz, MeOD)	δ 7.74 – 7.70 (m, 2H), 7.36 – 7.32 (m, 2H), 2.78 – 2.72 (m, 2H), 2.56 (pd, J = 6.4, 5.5 Hz, 1H), 2.41 (d, J = 0.8 Hz, 3H), 2.28 (s, 3H), 0.98 (d, J = 6.4 Hz, 3H)
¹³C NMR (126 MHz, MeOD)	δ 143.8, 140.2, 130.5, 128.0, 56.0, 49.5, 33.3, 21.4, 17.4
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₁H₁₉N₂O₂S 243.1162; Found 243.1161

tert-Butyl 4-Methylimidazolidine-1-carboxylate
¹H NMR (400 MHz, CDCl₃, 25 °C)	δ 4.54 – 4.26 (m, 1H), 4.13 (s, 1H), 3.48 (s, 1H), 3.32 (dt, J = 8.0, 6.2 Hz, 1H), 2.74 (s, 1H), 2.03 (d, J = 15.1 Hz, 1H), 1.45 (s, 9H), 1.24 (d, J = 6.4 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃, 25 °C)	δ 153.5, 79.6, 63.1, 54.6, 52.2, 28.6, 18.0
¹H NMR (500 MHz, DMSO, 80 °C)	δ 4.19 (d, J = 8.4 Hz, 1H), 3.95 (d, J = 8.4 Hz, 1H), 3.32 (dd, J = 9.6, 6.3 Hz, 1H), 3.23 – 3.15 (m, 1H), 3.14 – 3.01 (m, 1H), 2.64 (dd, J = 9.6, 7.7 Hz, 1H), 1.41 (s, 9H), 1.11 (d, J = 6.5 Hz, 3H)
¹³C NMR (126 MHz, DMSO, 80 °C)	δ 152.3, 77.8, 62.3, 53.1, 51.4, 27.9, 17.1
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₉H₁₉N₂O₂ 187.1441; Found 187.1442

Propane-1,2-diamine dihydrochloride
¹H NMR (500 MHz, MeOD)	δ 3.72 – 3.58 (m, 1H), 3.33 – 3.29 (m, 1H), 3.15 (dd, J = 13.3, 7.5 Hz, 1H), 1.44 (d, J = 6.7 Hz, 3H)
¹³C NMR (126 MHz, MeOD)	δ 46.6, 43.3, 16.6
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₃H₁₁N₂ 75.0917; Found 75.0917

1,5-Dimethylimidazolidin-2-one
¹H NMR (500 MHz, CDCl₃)	δ 4.45 (s, 1H), 3.69 – 3.56 (m, 1H), 3.50 (t, J = 8.3 Hz, 1H), 2.96 (td, J = 8.1, 1.2 Hz, 1H), 2.74 (s, 3H), 1.25 (d, J = 6.2 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 162.8, 54.0, 46.1, 28.2, 18.4
HRMS (ESI, m/z)	[M+Na]⁺ Calculated for C₅H₁₀N₂NaO 137.0685; Found 137.0685

tert-Butyl 4-Methyl-2,5-dihydro-1H-imidazole-1-carboxylate Borane Complex
¹H NMR (400 MHz, CDCl₃)	δ 5.21 (s, 2H), 4.45 (s, 2H), 2.33 (s, 3H), 1.47 (s, 9H)
¹³C NMR (101 MHz, CDCl₃)	δ 175.6, 152.3, 82.0, 76.2, 57.9, 28.4, 15.9
¹¹B NMR (128 MHz, CDCl₃)	δ -22.02 (d, J = 88.2 Hz)
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₉H₁₉BN₂NaO₂ 221.1432; Found 221.1432

5-Methyl-3-tosyl-6-oxa-1,3-diazabicyclo[3.1.0]hexane
¹H NMR (500 MHz, CDCl₃)	δ 7.68 – 7.61 (m, 2H), 7.38 – 7.29 (m, 2H), 4.67 (d, J = 13.4 Hz, 1H), 4.32 (d, J = 13.4 Hz, 1H), 3.90 (d, J = 13.5 Hz, 1H), 3.38 (d, J = 13.5 Hz, 1H), 2.43 (s, 3H), 1.52 (s, 3H)
¹³C NMR (126 MHz, CDCl₃)	δ 144.2, 134.7, 129.9, 127.8, 86.2, 71.1, 50.4, 21.8, 16.1
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₁H₁₅N₂O₃S 255.0798; Found 255.0798

N-(tert-Butyl)-4-methyl-1-tosyl-3-(2,2,2-trifluoroacetyl)imidazolidine-4-carboxamide
¹H NMR (400 MHz, CDCl₃)	δ 7.82 – 7.70 (m, 2H), 7.48 – 7.34 (m, 2H), 6.06 (s, 1H), 5.00 (d, J = 7.7 Hz, 1H), 4.81 (d, J = 7.8 Hz, 1H), 3.87 (d, J = 10.9 Hz, 1H), 3.41 (d, J = 10.9 Hz, 1H), 2.48 (s, 3H), 1.64 (s, 3H), 1.34 (s, 9H)
¹³C NMR (126 MHz, CDCl₃)	δ 168.2, 154.2 (q, J = 38.1 Hz), 145.3, 133.1, 130.4, 128.0, 115.7 (q, J = 287.9 Hz), 68.7, 63.2, 56.9, 52.1, 28.5, 21.8, 20.0
¹⁹F NMR (376 MHz, CDCl₃)	δ -73.14
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₈H₂₅F₃N₃O₄S 436.1512; Found 436.1511

4-Methyl-1-tosyl-1H-imidazole
¹H NMR (400 MHz, CDCl₃)	δ 7.91 (d, J = 1.4 Hz, 1H), 7.82 – 7.78 (m, 2H), 7.36 – 7.32 (m, 2H), 6.97 (p, J = 1.2 Hz, 1H), 2.43 (s, 3H), 2.17 (d, J = 1.1 Hz, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 146.18, 141.24, 136.24, 135.34, 130.48, 127.43, 113.45, 21.85, 13.73
HRMS (ESI, m/z)	[M+H]⁺ Calculated for C₁₁H₁₃N₂O₂S 237.0692; Found 237.0691