Synthesis of 5-(diethoxyphosphoryl)-substituted Hydrogenated Pyrimidine-2-thiones

Anatoly Shutalev; Anastasia Fesenko

doi:10.3390/ecsoc-11-01328

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Synthesis of 5-(diethoxyphosphoryl)-substituted Hydrogenated Pyrimidine-2-thiones

Anatoly D. Shutalev

^*,

Anastasia A. Fesenko

¹ Department of Organic Chemistry, M.V.Lomonosov State Academy of Fine Chemical Technology, 119571 Moscow, Russian Federation

Published: 30 November 2007 by MDPI in The 11th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-11-01328

Abstract: The reaction of sodium enolate of diethyl (2-oxoprop-1-yl)phosphonate with N-(1-tosylprop-1-yl)thiourea results in a 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.

Keywords: b-oxophosphonates, a-tosyl-substituted thioureas, thioureidoalkylation, 5-(diethoxyphosphoryl)-substituted hydrogenated pyrimidine-2-thiones, reduction, acyliminium cations

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Anatoly Shutalev

Anastasia Fesenko