(1,1'-Biphenyl)-4-carboxylic acid → HCID 11628130, compound

Participants

Reaction Conditions

Reaction Steps

0.2 g 3-(5-Amino-2-chloro-phenyl)-7-methanesulfonyl-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one were dissolved in 50 mL of dichloromethane. 0.137 g Biphenyl-4-carboxylic acid and 0.042 g 4-dimethylaminopyridine (DMAP) were added. The solution was cooled to 0° C. and 0.128 g N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (EDCI), dissolved in 20 mL dichloromethane were slowly added. The reaction mixture was stirred for 24 h under nitrogen. The reaction was quenched by extraction with 100 mL of an aqueous solution of potassium carbonate. The phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over sodium sulfate and evaporated. The crude product was purified by flash chromatography on silica gel (n-heptane/ethyl acetate (EtOAc)) to give the title product in 28% yield.

Provenance & Evidence