Triethylamine → 2-Chloro-N-(4,4-difluorocyclohexyl)-5,6-dimethylpyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

To the solution of 2,4-dichloro-5,6-dimethylpyrimidine (0.585 g, 3.304 mmol, Example 1, Step C) in N,N-dimethylformamide (10 mL), (4,4-difluorocyclohexyl)amine hydrochloride (0.652 g, 3.800 mmol) and triethylamine (1.338 g, 13.218 mmol) were added, and reaction mixture was heated at 50° C. overnight. Volatiles were removed under reduced pressure, and the residue was poured into water (300 mL). The mixture was extracted with ether (3×50 mL), dried over sodium sulfate, filtered, and concentrated. The residue was subjected to column chromatography on silica eluting with a mixture of hexane/ethyl acetate (gradient 4:1-2:1) to provide 621 mg (68%) of the titled compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.18-1.24 (m, 1H), 1.60-1.72 (m, 2H), 1.80-2.10 (m, 8H) 2.21 (s, 3H), 4.00-4.10 (m, 1H), 6.73 (d, J=7.79 Hz, 1H); MS (ESI) m/z 318.6 (M+1)+.

Provenance & Evidence