Hydrochloric Acid → 7-Cyclohexyl-6-[4-(3-methoxyphenyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Participants

Reaction Steps

To a solution of 47 mg (0.103 mmol) of 7-cyclohexyl-6-(3′-methoxy-biphenyl-4-yl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester in 3 mL of tetrahydrofuran was added 0.62 mL (0.62 mmol) of 1 M LiOH solution, and the resulting mixture was heated at reflux overnight. The reaction mixture was then acidified with 1 M HCl solution to pH=2, and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, and concentrated to give a residue which was purified via reverse-phase chromatography to afford (after lyophilization) 15 mg (34% yield) of 7-cyclohexyl-6-(3′-methoxy-biphenyl-4-yl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (446) as a solid (90% purity) as indicated by 1H NMR; LC-MS—calcd for C26H25N3O3 [M++H]+: 428.19, found: 428.2.

Provenance & Evidence