Diisopropylethylamine → 2-Amino-4-[(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)-ethylamino]-pyrimidine-5-carbonitrile

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A mixture of (S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine.2HCl (85 mg, 0.259 mmol), 2-amino-4-chloropyrimidine-5-carbonitrile (40 mg, 0.26 mmol) and DIPEA (222 μL, 1.29 mmol) in IPA (0.75 mL) was heated at 90° C. in a sealed vial for 21 h. After cooling to RT, the crude mixture was diluted with MeOH and loaded into an Isolute®SCX-2 cartridge. The cartridge was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined, concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in DCM) followed by trituration from EtOAc/Et2O/cyclohexane to afford 362 as a white solid (61 mg, 63%). LCMS (Method K): RT 3.47 min [M+H]+ 374.02. 1H NMR (DMSO-d6, 400 MHz): δ 8.08 (1H, s), 7.74 (1H, dd, J=8.80, 4.85 Hz), 7.68 (1H, d, J=7.49 Hz), 7.58-7.52 (5H, m), 7.16-6.70 (4H, m), 5.51 (1H, m), 1.47 (3H, d, J=6.80 Hz)

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