Hydrochloric Acid → HCID 73297045, compound

Participants

Reaction Steps

Ammonium acetate (0.587 g, 7.61 mmol) was added to a solution of 1-(2-(2-(2-((6-Acetylpyridin-3-yl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide 32 (0.166 g, 0.381 mmol) in MeOH (5 mL) and THF (5 mL) and the mixture was stirred for 20 minutes under a nitrogen atmosphere. Sodium cyanoborohydride (0.017 g, 0.27 mmol) was added and the mixture was stirred for 5 hours. Additional sodium cyanoborohydride (0.017 g, 0.27 mmol) was added and the mixture was stirred for 22 hours at 35° C. Water (10 mL) was added to the mixture which was then acidified with 20% aqueous hydrochloride (10 mL). The aqueous phase was washed with Et2O (2×30 mL) and then basified with solid potassium hydroxide to pH 10. The aqueous phase was extracted with DCM (3×30 mL) and the combined organics were washed with brine, dried (Na2SO4), adsorbed onto silica and purified by silica column chromatography (Combiflash Rf, 12 g SiO2 Cartridge, 0-30% MeOH in DCM) to give the title compound 33 as a white solid (0.101 g, 60%). LCMS-B: rt 4.32 min; m/z 437 [M+H]+.

Provenance & Evidence