Pyridine → HCID 21998647, compound

Participants

Reaction Steps

To a well stirred solution of (+)-5-benzyloxycarbonyl-1,6-dihydro-2-methoxy-4-methoxymethyl-6-(3,4-difluorophenyl)pyrimidine (1.25 g, 3.0 mmol) and pyridine (2 mL) in CH2Cl2 (20 mL) was added powdered 4-nitrophenyl chloroformate (1 g, 5 mmol) at room temperature. Solvent was evaporated and the residue was purified by column chromatography on silica gel using CHCl3/EtOAc (20%-50%) as the eluent to give (+)-5-benzyloxycarbonyl-4-methoxymethyl-1,6-dihydro-2-methoxy-6-(3,4-difluorophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidine (1.70 g, 86%) as a viscous oil. [α]D=+200 (c=1.215 g in 100 mL CHCl3) g) (+)-6-(3,4-Difluorophenyl)-1-{N-[2-(4-cyano-4-phenylcyclohex-1-ylamino)-ethyl]}carboxamido-5-benzyloxycarbonyl-4-methoxymethyl-2-oxo 1,2,3,6-tetrahydropyrimidine (cis isomer).

Provenance & Evidence