Dimethylformamide → 3-(1-cyano-1-methylethyl)-N-[4-methyl-3-({2-[(morpholin-4-ylacetyl)amino][1,3]thiazolo[5,4-d]pyrimidin-5-yl}amino)phenyl]benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-d]pyrimidin-5-yl}amino)-4-methylphenyl]-3-(1-cyano-1-methylethyl)benzamide (152 mg, 292 μmol) in tetrahydrofuran (4 mL)/N,N-dimethylformamide (0.5 mL) were added triethylamine (121 μL, 876 μmol) and morpholine (76 μL, 876 μmol), and the mixture was stirred at 60° C. for 15 hr. To the reaction mixture was added water (15 mL), and the mixture was extracted with ethyl acetate (20 mL, 5 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 basic silica gel column chromatography (ethyl acetate/methanol=100/0→97/3), and the fractions containing the object product were concentrated under reduced pressure. The obtained residue was recrystallized from tetrahydrofuran and hexane to give the title compound (131 mg, 78%) as colorless crystals.

Provenance & Evidence