Synthesis and 1,3-dimethylation of 5-ethoxycarbonyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one

Keywords: 3,4-dihydropyrimidin-2(1H)-one, alkylation, Reformatsky reaction, Biginelli reaction

Abstract

1,3-Dimethylation of 5-ethoxycarbonyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one can be carried out in one stage, using the system DMF–NaH and the excess of MeI. It is shown, that 5-ethoxycarbonyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one can be obtained with a good yield (55%) by reflux of ethyl 3,3-diethoxypropanoate, urea and benzaldehyde in acetic acid. The conditions of the protocol for the synthesis of ethyl 3,3-diethoxypropanoate starting from bromoacetic ester and ortho-formic ester by modified Reformatsky reaction have been optimized.

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Published
2012-12-03
Cited
How to Cite
Kolosov, M. A., Al-Ogaili, M., & Orlov, V. D. (2012). Synthesis and 1,3-dimethylation of 5-ethoxycarbonyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one. Kharkiv University Bulletin. Chemical Series, (21), 108-111. https://doi.org/10.26565/2220-637X-2012-21-07

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