Ethyl 2-[(3-methoxyphenyl)methylidene]-3-oxobutanoate → HCID 131717850, compound

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A mixture of 2-[(3-methoxyphenyl)methylene]-3-oxobutanoic acid, ethyl ester (2.0 g., 8 mmole), S-(4-methoxybenzyl)thiopseudourea, hydrochloride (1.87 g., 8 mmole), and sodium acetate (0.67 g., 8 mmole) in dimethylformamide (10 ml.) is stirred at 70° for 4 hours. The cooled mixture is diluted with ether and washed with water, sodium bicarbonate, and brine. The dried solution is evaporated to give 2.85 g. of an impure oil. Flash chromatography using ethyl acetate:hexanes (1:3) gives 2.0 g. of 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-4-(3-methoxyphenyl)- 6-methyl-5-pyrimidinedicarboxylic acid, ethyl ester as an oil.

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