Parallel synthesis of 2-substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides

Molecules. 2012 May 8;17(5):5363-84. doi: 10.3390/molecules17055363.

Abstract

A library of 24 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides 10{1,2; 1-12} was prepared by a parallel solution-phase approach. The synthesis comprises a five-step transformation of itaconic acid (11) into 1-methyl and 1-phenyl substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxylic acids 17{1,2} followed by parallel amidation of 17{1,2} with a series of 12 aliphatic amines 18{1-12} to afford the corresponding carboxamides 10 in good overall yields and in 80-100% purity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amines / chemistry
  • Carboxylic Acids / chemistry
  • Combinatorial Chemistry Techniques
  • Magnetic Resonance Spectroscopy
  • Pyrimidines / chemical synthesis*
  • Succinates / chemistry

Substances

  • Amides
  • Amines
  • Carboxylic Acids
  • Pyrimidines
  • Succinates
  • itaconic acid