Hydrochloric Acid → 7-(2,4-Dimethoxybenzyl)-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-1,2,3,5,6,7-hexahydropyrido[3,4-d]pyrimidine-4,8-dione

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Reaction Steps

To a solution of 1-isothiocyanato-4-(2,2,2-trifluoroethoxy)benzene (115 mg) in N,N-dimethylformamide (2 ml) was added sodium hydride (60% in oil, 45 mg), and a solution of ethyl 5-amino-1-(2,4-dimethoxybenzyl)-6-oxo-1,2,3,6-tetrahydropyridine-4-carboxylate (150 mg) in N,N-dimethylformamide (2 ml) was added dropwise thereto over 5 min under ice-cooling. The mixture was stirred for 10 min, allowed to be warmed to room temperature, and stirred for 30 min. The reaction mixture was poured into 0.5M hydrochloric acid (4 ml) under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained yellow solid was washed with diethyl ether to give the title compound (70 mg) as beige fine needle crystals.

Provenance & Evidence