(+)-5-Methoxycarbonyl-4-methoxymethyl-1,2,3,6-tetrahydro 2-oxo-6-(3,4-difluorophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidine → 4-(3,4-Difluorophenyl)-6-methoxymethyl-2-oxo-3-[3-(4-phenyl-4-(furan-2-yl)piperidin-1-yl)propyl]carbamoyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(3,4-difluorophenyl)-4-methoxymethyl-2-oxo-3,6-dihydro-2H-pyrimidine-1,5-dicarboxylic acid 5-methyl ester 1-(4-nitrophenyl)ester (20 mg, 0.04 mmol) in 2 ml of CH2Cl2 was added 3-(4-phenyl-4-furan-2-yl-piperidin-1-yl)-propylamine (12 mg, 0.04 mmol) and resulting solution was stirred for 2 h at 25° C. The reaction mixture was concentrated in vacuo to provide an oil which was subjected to column chromatography over silica gel (5% MeOH/CHCl3) to yield 22 mg (85%) of the desired product, which was converted to HCl salt and recrystallized from EtOAC-Et2O to afford 18 mg of the product as a white solid: mp 153-155° C.; Anal. Calc. For C33H36F2N4O6 requires C, 60.1; H, 5.46; N, 8.49. Found: C, 58.9; H, 5.53; 8.45.

Provenance & Evidence