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

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Reaction Steps

To a solution of 2-{[5-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)-2-methylphenyl]amino}-5-nitropyrimidin-4-yl thiocyanate (1.09 mmol, 515 mg) in 1-methylpyrrolidin-2-one (9 mL)/ethanol (6 mL) were added 10% palladium-carbon (120 mg) and acetic acid (0.5 mL), and the mixture was stirred at room temperature under a hydrogen atmosphere (3.0 atm) for 19 hr. The insoluble material was filtered off, saturated aqueous sodium hydrogen carbonate solution (30 mL) was added, and the mixture was extracted with ethyl acetate (30 mL, 20 ml). The combined organic layer was washed with saturated brine (10 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=40/60→10/90), and the fractions containing the object product were concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate and hexane to give the title compound (281 mg, 58%) as purple crystals.

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