This article is cited in 21 papers

Synthesis of diethyl 2-thioxo-1,2,3,4-tetrahydroand hexahydropyrimidine-5-phosphonates

A. A. Fesenko, D. A. Cheshkov, A. D. Shutalev

M.V. Lomonosov Institute of Fine Chemical Technologies, MIREA - Russian Technological University, Moscow, Russian Federation

Abstract: The reaction of sodium enolate of diethyl (2-oxoprop-1-yl)phosphonate with N-(1-tosylprop-1-yl)thiourea results in the stereoselective formation of diethyl (4R*,5R*,6R*)-6-ethyl-4-hydroxy-4-methyl-2-thioxohexahydropyrimidine-5-phosphonate, which is transformed into diethyl 4-ethyl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-phosphonate and diethyl (4R*,5S*,6R*)-4-ethyl-6-methyl-2-thioxohexahydropyrimidine-5-phosphonate by acid-catalysed dehydration and stereoselective reduction with NaBH₄–CF₃COOH, respectively.

Language: English

DOI: 10.1016/j.mencom.2008.01.019

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