Microwave-assisted combinatorial synthesis of new 3-pyrimidin-5-ylpropanamides via a solvent-dependent chemoselective reaction

J Comb Chem. 2009 Mar 9;11(2):310-4. doi: 10.1021/cc800175n.

Abstract

A series of new 3-pyrimidin-5-ylpropanamides was selectively synthesized via a microwave-assisted, chemoselective reaction of arylidene-Meldrum's acid, 6-hydroxypyrimidin-4(3H)-one, and structurally diverse amines including (S or R)-1-phenylethanamine, cyclohexanamine, and cyclopentanamine depended on nature of solvents. In this reaction, the utilization of HOAc as a solvent leads to 3-pyrimidin-5-ylpropanamides, whereas water as reaction media results in the spiro[5.5]undecane-1,5,9-triones from same starting materials. This method has the advantages of short synthetic route, operational simplicity, increased safety for small-scale high-speed synthesis, and minimal environment impact.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Combinatorial Chemistry Techniques / methods*
  • Microwaves*
  • Molecular Structure
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Solvents / chemistry

Substances

  • 3-pyrimidin-5-ylpropanamide
  • Amides
  • Pyrimidines
  • Solvents