Open AccessEthyl 2‐({6‐amino‐2‐(benzylsulfanyl)‐5‐[2‐(ethoxycarbonyl)prop‐2‐enyl]pyrimidin‐4‐yloxy}methyl)acrylate
Author(s) -
Gibson Colin L.,
Huggan Judith K.,
Kennedy Alan R.,
Suckling Colin J.
Publication year - 2006
Publication title -
acta crystallographica section e
Language(s) - English
Resource type - Journals
ISSN - 1600-5368
DOI - 10.1107/s1600536805041899
Subject(s) - acrylate , chemistry , thio , claisen rearrangement , conformational isomerism , carbon fibers , medicinal chemistry , stereochemistry , double bond , ethyl acrylate , polymer chemistry , organic chemistry , molecule , materials science , composite material , polymer , monomer , composite number
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, C 23 H 27 N 3 O 5 S. 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.