Sodium Bicarbonate → Tert-butyl (3-(2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxamido)propyl)carbamate

Participants

Reaction Steps

To 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylic acid (C5, 328 mg), N-Boc-1,3-propanediamine (289 μL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (846 mg), and 1-hydroxybenzotriazole monohydrate (676 mg), N,N-dimethylformamide (10 mL) and triethylamine (306 μL) were added at room temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluent, 50 to 30% hexane in ethyl acetate) to obtain tert-butyl (3-(2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxamido)propyl)carbamate (D1, 224 mg) as white solid.

Provenance & Evidence