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
Full text not available in this repository. (Request a copy from the Strathclyde author)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.
| Item type: | Article |
|---|---|
| ID code: | 731 |
| Keywords: | pyrimidines, phenyl, Chemistry |
| Subjects: | Science > Chemistry |
| Department: | Faculty of Science > Pure and Applied Chemistry Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences |
| Related URLs: | |
| Depositing user: | Catriona Mccallum |
| Date Deposited: | 07 Apr 2006 |
| Last modified: | 12 Mar 2012 10:35 |
| URI: | http://strathprints.strath.ac.uk/id/eprint/731 |
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