Diisopropylethylamine → 2-Amino-4-methyl-6-[1-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethylamino]-pyrimidine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)ethylamine (66 mg, 0.28 mmol), 2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile (38 mg, 0.23 mmol) and DIPEA (142 μL, 0.831 mmol) in IPA (1 mL) was heated at 90° C. in a sealed vial for 18 h. After cooling to RT, the reaction 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 50-100% EtOAc in cyclohexane) followed by trituration from EtOAc to afford 366 as an off-white solid (41 mg, 40%). LCMS (Method K): RT 2.54 min [M+H]+ 371.10. 1H NMR (DMSO-d6, 400 MHz): δ 8.25 (1H, dd, J=4.77, 1.47 Hz), 8.14 (1H, dd, J=7.98, 1.47 Hz), 7.55-7.44 (6H, m), 7.33 (1H, m), 7.12-6.61 (2H, m), 5.52 (1H, m), 2.21 (3H, s), 1.47 (3H, d, J=6.81 Hz)

Provenance & Evidence