A diversity-oriented synthesis of 3-(2-amino-1,6-dihydro-6-oxo-pyrimidin-5- yl)propanoic esters

Xavier Berzosa; Sofia Pettersson; Jordi Teixidó; José I. Borrell

doi:10.1007/s11030-010-9287-9

A diversity-oriented synthesis of 3-(2-amino-1,6-dihydro-6-oxo-pyrimidin-5- yl)propanoic esters

Xavier Berzosa
, Sofia Pettersson
, Jordi Teixidó
, José I. Borrell^*

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

2 Citations (Scopus)

Abstract

The synthesis of dimethyl 2-(methoxymethylene) pentanedioates by an unusual Michael addition of 3,3-dimethoxypropionate to α, β-unsaturated esters is described. These new intermediates can subsequently be converted to methyl 3-(2-amino-1,6-dihydro-6-oxo-pyrimidin-5-yl)propanoates upon treatment with guanidine carbonate. The resulting pyrimidine derivatives are open-chain analogues of pyrido[2,3-d]pyrimidines with interesting biological activities.

Original language	English
Pages (from-to)	595-601
Number of pages	7
Journal	Molecular Diversity
Volume	15
Issue number	2
DOIs	https://doi.org/10.1007/s11030-010-9287-9
Publication status	Published - May 2011

Keywords

Methyl 3,3-dimethoxypropionate
Michael addition
Microwave synthesis
Pyrimidin-5-ylpropanoic acids
α,β-Unsaturated ester

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10.1007/s11030-010-9287-9

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title = "A diversity-oriented synthesis of 3-(2-amino-1,6-dihydro-6-oxo-pyrimidin-5- yl)propanoic esters",

abstract = "The synthesis of dimethyl 2-(methoxymethylene) pentanedioates by an unusual Michael addition of 3,3-dimethoxypropionate to α, β-unsaturated esters is described. These new intermediates can subsequently be converted to methyl 3-(2-amino-1,6-dihydro-6-oxo-pyrimidin-5-yl)propanoates upon treatment with guanidine carbonate. The resulting pyrimidine derivatives are open-chain analogues of pyrido[2,3-d]pyrimidines with interesting biological activities.",

keywords = "Methyl 3,3-dimethoxypropionate, Michael addition, Microwave synthesis, Pyrimidin-5-ylpropanoic acids, α,β-Unsaturated ester",

author = "Xavier Berzosa and Sofia Pettersson and Jordi Teixid{\'o} and Borrell, \{Jos{\'e} I.\}",

note = "Funding Information: Acknowledgment X. Berzosa is grateful for a fellowship from Generalitat de Catalunya (2006{\textendash}2009, grant 2006FI 00058).",

year = "2011",

month = may,

doi = "10.1007/s11030-010-9287-9",

language = "English",

volume = "15",

pages = "595--601",

journal = "Molecular Diversity",

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T1 - A diversity-oriented synthesis of 3-(2-amino-1,6-dihydro-6-oxo-pyrimidin-5- yl)propanoic esters

AU - Berzosa, Xavier

AU - Pettersson, Sofia

AU - Teixidó, Jordi

AU - Borrell, José I.

N1 - Funding Information: Acknowledgment X. Berzosa is grateful for a fellowship from Generalitat de Catalunya (2006–2009, grant 2006FI 00058).

PY - 2011/5

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N2 - The synthesis of dimethyl 2-(methoxymethylene) pentanedioates by an unusual Michael addition of 3,3-dimethoxypropionate to α, β-unsaturated esters is described. These new intermediates can subsequently be converted to methyl 3-(2-amino-1,6-dihydro-6-oxo-pyrimidin-5-yl)propanoates upon treatment with guanidine carbonate. The resulting pyrimidine derivatives are open-chain analogues of pyrido[2,3-d]pyrimidines with interesting biological activities.

AB - The synthesis of dimethyl 2-(methoxymethylene) pentanedioates by an unusual Michael addition of 3,3-dimethoxypropionate to α, β-unsaturated esters is described. These new intermediates can subsequently be converted to methyl 3-(2-amino-1,6-dihydro-6-oxo-pyrimidin-5-yl)propanoates upon treatment with guanidine carbonate. The resulting pyrimidine derivatives are open-chain analogues of pyrido[2,3-d]pyrimidines with interesting biological activities.

KW - Methyl 3,3-dimethoxypropionate

KW - Michael addition

KW - Microwave synthesis

KW - Pyrimidin-5-ylpropanoic acids

KW - α,β-Unsaturated ester

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DO - 10.1007/s11030-010-9287-9

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AN - SCOPUS:80051573512

SN - 1381-1991

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JO - Molecular Diversity

JF - Molecular Diversity

IS - 2

ER -

A diversity-oriented synthesis of 3-(2-amino-1,6-dihydro-6-oxo-pyrimidin-5- yl)propanoic esters

Abstract

Keywords

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