Water → N-[3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-d]pyrimidin-5-yl)amino)-4-methylphenyl]-3-(1-cyano-1-methylethyl)benzamide

Participants

Reaction Steps

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)amino]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (948 mg, 2.14 mmol) produced in Example D25(iii) in N,N-dimethylacetamide (20 mL) was added chloroacetyl chloride (425 μL, 5.34 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added water (60 mL), and the mixture was extracted with ethyl acetate (30 mL, 15 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=60/40→30/70), and the fractions containing the object product were concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to give the title compound (778 mg, 71%) as a white solid.

Provenance & Evidence