(+)-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-(thiophen-2-yl)piperidin-1-yl)-propylcarbamoyl}-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 (29 mg, 0.06 mmol) in 2 ml of CH2Cl2 was added 3-(4-phenyl-4-thiophen-2-yl-piperidin-1-yl)propylamine (20 mg, 0.07 mmol) and the 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 25 mg (64%) of the desired product which was converted to a HCl salt and recrystallized from EtOAC-Et2O to afford 22 mg of the product as a white solid: mp 157-159° C.; Anal. Calc. For C33H36F2N4O5S requires C, 58.6; H, 5.33; N, 8.29. Found: C, 57.3; H, 5.45; 7.90.

Provenance & Evidence