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 (http://www.blackwell-synergy.com/doi/full/10.1107/...)
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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.
ORCID iDs
Gibson, C.L. ORCID: https://orcid.org/0000-0003-4948-1266, Huggan, J.K., Kennedy, A.R. ORCID: https://orcid.org/0000-0003-3652-6015 and Suckling, C.J.;-
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Item type: Article ID code: 731 Dates: DateEventJanuary 2006PublishedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry
Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical SciencesDepositing user: Users 45 not found. Date deposited: 07 Apr 2006 Last modified: 02 Sep 2024 00:38 URI: https://strathprints.strath.ac.uk/id/eprint/731