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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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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.