Hydrochloric Acid → HCID 131717851, compound

Participants

Reaction Steps

A solution of 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, 1,1-dimethylethyl ester (28 g., 96.12 mmole) in dimethylformamide (98 ml.) is treated with S-(4-methoxybenzyl)thiopseudourea, hydrochloride (22.37 g., 96.12 mmole) and sodium acetate (7.9 g., 96.12 mmole). The mixture is heated at 60° overnight, diluted with ether, and filtered to remove sodium chloride. The filtrate is washed with water (150 ml.), sodium bicarbonate (150 ml.), and brine. The organic layer is dried over anhydrous magnesium sulfate, filtered, and stripped to give an oil. This oil is dissolved in dichloromethane (300 ml.) and treated with methanolic hydrochloric acid (1 eq., 96.12 mmole) to crystallize out 41.74 g. of product. A second crop of 2.77 g. is collected by reducing the volume of the mother liquor and cooling at 0° overnight to give a total of 44.51 g. of white solid 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1,1-dimethylethyl ester; m.p. 192°. TLC (silica gel; ethyl acetate:hexanes, 1:2 Rf =0.51.

Provenance & Evidence