Diisopropylethylamine → 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-N-(1-methyl-4-piperidyl)-3H-benzofuran-4-carboxamide

Participants

Reaction Steps

7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylic acid 4f (931 mg, 2 mmol) was dissolved in 50 mL of dichloromethane followed by the addition of 1-methyl-piperidyl-4-yl-amine (228 mg, 2 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (642 mg, 2 mmol) and diisopropylethylamine (775 mg, 6 mmol). The reaction solution was stirred for 1.5 hours. The resulting mixture was added with 50 mL of saturated sodium bicarbonate solution, extracted with dichloromethane (50 mL×3). The combined organic phase was washed with water (15 mL), saturated sodium chloride solution (15 mL) successively, dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-N-(1-methyl-4-piperidyl)-3H-benzofuran-4-carboxamide 4 (793 mg, yield: 70.8%) as a white solid.

Provenance & Evidence