Studies on the Pyrimidine Derivatives. XXXI. Reactions of Ethyl 2-Methoxymethylene-3-ethoxypropionate with Ureas

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Ethyl 2-methoxymethylene-3-ethoxypropionate (III) undergoes condensation with urea, and N-substituted urea in ethanol solution in the presence of hydrochloric acid. With urea, III gave ethyl 2-oxo-1, 2, 3, 4-tetrahydro-5-pyrimidinecarboxylate (V), with N-methyl-urea a mixture of ethyl 2-oxo-methyl-1, 2, 3, 4-tetrahydro-5-pyrimidinecarboxylate (XIII) and its isomeric 1-methyl compound (XIV), which was separated into each isomer, and with N-phenylurea the 1-phenyl compound (XV) was exclusively obtained. Conversion into pyrimidines was achieved by dehyrogenation and subsequent chlorination of V.

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