Ethyl 2-({6-amino-2-(benzylsulfanyl)-5-[2-(ethoxycarbonyl)prop-2-enyl]pyrimidin-4-yloxy}methyl)acrylate

C.L. Gibson; J.K. Huggan; A.R. Kennedy; C.J. Suckling

doi:10.1107/S1600536805041899

Ethyl 2-({6-amino-2-(benzylsulfanyl)-5-[2-(ethoxycarbonyl)prop-2-enyl]pyrimidin-4-yloxy}methyl)acrylate

C.L. Gibson, J.K. Huggan, A.R. Kennedy, C.J. Suckling

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	o324-o326
Journal	Acta Crystallographica Section E: Structure Reports
Volume	62
Issue number	1
DOIs	https://doi.org/10.1107/S1600536805041899
Publication status	Published - Jan 2006

Keywords

pyrimidines
phenyl

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10.1107/S1600536805041899

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title = "Ethyl 2-({6-amino-2-(benzylsulfanyl)-5-[2-(ethoxycarbonyl)prop-2-enyl]pyrimidin-4-yloxy}methyl)acrylate",

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.",

keywords = "pyrimidines, phenyl",

author = "C.L. Gibson and J.K. Huggan and A.R. Kennedy and C.J. Suckling",

year = "2006",

month = jan,

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language = "English",

volume = "62",

pages = "o324--o326",

journal = "Acta Crystallographica Section E: Structure Reports",

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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

JF - Acta Crystallographica Section E: Structure Reports

SN - 1600-5368

IS - 1

ER -

Ethyl 2-({6-amino-2-(benzylsulfanyl)-5-[2-(ethoxycarbonyl)prop-2-enyl]pyrimidin-4-yloxy}methyl)acrylate

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Ethyl 2-({6-amino-2-(benzylsulfanyl)-5-[2-(ethoxycarbonyl)prop-2-enyl]pyrimidin-4-yloxy}methyl)acrylate

Abstract

Keywords

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