1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-(3,4-Difluorophenyl)-1,6-dihydro-5-(3-(4-methoxycarbonyl-4-phenylpiperidin-1-yl)propylaminocarbonyl)-1-methoxymethyl-2,4-dimethylpyrimidine

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Reaction Steps

A mixture of 5-carboxy-6-(3,4-difluoro-phenyl)-1,6-dihydro-1-methoxymethyl-2,4-dimethylpyrimidine (0.13 g, 0.42 mmol.), 4-dimethylaminopyridine (0.1 g, 0.84 mmol.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.16 g, 0.82 mmol.) and CH2Cl2 (5 mL) was stirred at room temperature for 0.5 hr. After the addition of 3-(4-methoxycarbonyl-4-phenylpiperidin-1-yl)propylamine (0.17 g, 0.62 mmol.), the mixture was refluxed overnight. To the mixture was added another 25 mL of CH2Cl2 and washed with saturated NH4Cl solution. After removal of the solvent, the residue was flash chramotographed over silica gel (eluent: 80:20 v/v ethyl acetate-methanol) to give the title compound in 32% yield (0.075 g) as a pale yellow solid: mp 53-57° C. Anal. Calcd. for C31H38F2N4O4.0.25CHCl3: C, 62.71; H, 6.44; N, 9.36. Found: C, 62.62; H, 6.79; N, 9.19.

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