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The Strathprints institutional repository is a digital archive of University of Strathclyde's Open Access research outputs. Strathprints provides access to thousands of Open Access research papers by University of Strathclyde researchers, including by researchers from the Department of Computer & Information Sciences involved in mathematically structured programming, similarity and metric search, computer security, software systems, combinatronics and digital health.

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Ethyl 2-({6-amino-2-(benzylsulfanyl)-5-[2-(ethoxycarbonyl)prop-2-enyl]pyrimidin-4-yloxy}methyl)acrylate

Gibson, C.L. and Huggan, J.K. and Kennedy, A.R. and Suckling, C.J. (2006) Ethyl 2-({6-amino-2-(benzylsulfanyl)-5-[2-(ethoxycarbonyl)prop-2-enyl]pyrimidin-4-yloxy}methyl)acrylate. Acta Crystallographica Section E: Structure Reports, 62 (1). o324-o326. ISSN 1600-5368

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Abstract

A new synthesis of carbon-carbon bonds at the 5-position of 2-thio­substituted pyrimidines via the Claisen rearrangement is reported. A direct route towards the synthesis of carbon bonds at the 5-position of 2-thio­benzyl pyrimidines when reacted with ethyl 2-(bromo­meth­yl)acrylate at 328 K delivered the unexpected title compound, C23H27N3O5S. Structural elucidation showed this compound to have undergone O-allyl­ation followed by ortho-Claisen rearrangement and subsequent secondary O-allyl­ation with excess ethyl 2-(bromo­meth­yl)acrylate. Disorder about the centre of symmetry allows it to exist as two conformers with different orientations of the phenyl group.