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

Mol Divers. 2011 May;15(2):595-601. doi: 10.1007/s11030-010-9287-9. Epub 2010 Nov 12.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Esters
  • Propionates / chemical synthesis
  • Propionates / chemistry*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Structure-Activity Relationship

Substances

  • Esters
  • Propionates
  • Pyrimidines
  • pyrimidine