Abstract
| Language | English |
|---|---|
| Pages | o324-o326 |
| Journal | Acta Crystallographica Section E: Structure Reports |
| Volume | 62 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Jan 2006 |
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Keywords
- pyrimidines
- phenyl
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Ethyl 2-({6-amino-2-(benzylsulfanyl)-5-[2-(ethoxycarbonyl)prop-2-enyl]pyrimidin-4-yloxy}methyl)acrylate. / Gibson, C.L.; Huggan, J.K.; Kennedy, A.R.; Suckling, C.J.
In: Acta Crystallographica Section E: Structure Reports, Vol. 62, No. 1, 01.2006, p. o324-o326.Research output: Contribution to journal › Article
TY - JOUR
T1 - Ethyl 2-({6-amino-2-(benzylsulfanyl)-5-[2-(ethoxycarbonyl)prop-2-enyl]pyrimidin-4-yloxy}methyl)acrylate
AU - Gibson, C.L.
AU - Huggan, J.K.
AU - Kennedy, A.R.
AU - Suckling, C.J.
PY - 2006/1
Y1 - 2006/1
N2 - 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.
AB - 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.
KW - pyrimidines
KW - phenyl
UR - http://www.blackwell-synergy.com/doi/full/10.1107/S1600536805041899
U2 - 10.1107/S1600536805041899
DO - 10.1107/S1600536805041899
M3 - Article
VL - 62
SP - o324-o326
JO - Acta Crystallographica Section E: Structure Reports
T2 - Acta Crystallographica Section E: Structure Reports
JF - Acta Crystallographica Section E: Structure Reports
SN - 1600-5368
IS - 1
ER -