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

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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 languageEnglish
Pages (from-to)595-601
Number of pages7
JournalMolecular Diversity
Volume15
Issue number2
DOIs
Publication statusPublished - May 2011

Keywords

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

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