Hydrochloric Acid → HCID 73056321, compound

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Reaction Steps

Ammonium acetate (0.339 g, 4.40 mmol) was added to a solution of 2-(2-(2-(2-((3-acetylphenyl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)acetamide (A141) (0.120 g, 0.293 mmol) in MeOH (5 mL) and the mixture was stirred for 20 minutes under a nitrogen atmosphere. Sodium cyanoborohydride (0.013 g, 0.21 mmol) was added and the mixture was stirred for 6 hours. Additional sodium cyanoborohydride (0.013 g, 0.21 mmol) was added and the mixture was stirred for 16 hours at room temperature. The mixture was diluted with water (10 mL), acidified with 20% aqueous HCl (10 mL) and washed with Et2O (2×30 mL). The aqueous phase was basified with solid potassium hydroxide to pH 10 and extracted with DCM (3×30 mL). The combined organic phases were washed with water, brine, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was adsorbed onto silica gel and purified by column chromatography (CombiFlash Rf, 12 g SiO2 Cartridge, 0-30% MeOH in DCM) to give the title compound (38) as a white foam (0.057 g, 47%). LCMS-B: rt 5.45 min; m/z 410 [M+H]+.

Provenance & Evidence