Diethyl (ethoxymethylene)malonate → 6-Oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester

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Reaction Steps

Diethyl ethoxymethylenemalonate (10.1 mL, 50 mmole) and formamidine acetate (10.4 g, 100 mmole) were refluxed in ethanol (10 mL) for 24 hours. The reaction mixture was allowed to cool to room temperature overnight, and suspended in ethyl acetate (30 mL) and 1.0N HCl (20 mL). The suspension was filtered, and the filter cake was washed with 1.0N HCl, followed by water, then ethyl acetate, and air dried affording the title compound as an tan:solid (3.33 g, 40% yield). Rf=0.21 (silica gel, 10% methanol in dichloromethane); m.p. 187-188° C.

Provenance & Evidence