Water → HCID 58459156, compound

Participants

Reaction Conditions

Reaction Steps

1-(-(3,5-Difluorophenyl)-3H-imidazo[4,5-b]pyridin-2-yl)ethylamine (600 mg, 2.18 mmol) and 4-chloro-pyrimidine-5-carbonitrile (300 mg, 2.18 mmol) were dissolved in n-butanol (30 mL). After the addition of DIPEA (422 mg, 3.28 mmol) the reaction mixture was heated at 120° C. overnight. The mixture was cooled to rt and water (50 mL) was added. The mixture was extracted with EtOAc (300 mL), dried over sodium sulfate and concentrated in vacuo to provide a crude product. The crude product was purified by column chromatography using 100-200 mesh silica gel and 0-50% EtOAc in hexane to provide 4-amino-6-(1-(3-(3,5-difluorophenyl)-3H-imidazo[4,5-b]pyridin-2-yl)-ethylamino)pyrimidine-5-carbonitrile: 1H NMR (400 MHz, DMSO-d6) δ 1.580 (d, J=6.8 Hz, 3H), 5.683-5.753 (m, 1H), 7.205 (br s, 2H), 7.307-7.367 (m, 4H), 7.768 (d, J=8 Hz, 1H), 7.888 (s, 1H), 8.149-8.172 (m, 1H), 8.276-8.292 (m, 1H); LC-MS (ESI) m/z 393.0 [M+H]+.

Provenance & Evidence