Hydrochloric Acid → HCID 178519970, compound

Participants

Reaction Steps

To a stirred solution of 5-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxy-N-phenylpyrimidine-4-carboxamide (47) (287 mg, 427 μmol, Eq: 1.00) in tetrahydrofuran (10 ml) was added HCl (1N) (640 μl, 640 μmol, Eq: 1.5) at room temperature and the reaction mixture was stirred for 6 hrs, neutralized with 1N NaOH aqueous solution, extracted with ethyl acetate, dried (MgSO4), concentrated, and chromatographed (silica gel, gradient, 0 to 5% methanol-dichloromethane) to obtain 5-(benzyloxy)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxy-N-(2-hydroxyethyl)-N-phenylpyrimidine-4-carboxamide (48) (white foam, 179 mg, 321 μmol, 75.1% yield).

Provenance & Evidence