Diethyl allylmalonate → 5-Allylpyrimidine-4,6-diol

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Reaction Steps

2-Allyl-malonic acid diethyl ester (Preparation 205, 100 g, 0.5 mol) was added dropwise to a mixture of sodium methoxide (27 g, 0.5 mol) in ethanol (1 L) at 0-5° C. and the mixture was stirred at this temperature for 10 min. Formamidine acetate (51.9 g, 0.5 mol) was added and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo, and aqueous hydrochloric acid (36.5%) and water were added to adjust the pH to approximately 3 at 0-20° C. The resulting mixture was filtered to afford the title compound as a colorless solid in 57% yield, 87.12 g.

Provenance & Evidence