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.
|Journal||Acta Crystallographica Section E: Structure Reports|
|Publication status||Published - Jan 2006|