New one-pot four-component synthesis of disubstituted pyrido[2,3-d]pyrimidine-6-carboxamide derivatives

J Comb Chem. May-Jun 2009;11(3):375-7. doi: 10.1021/cc800189j.

Abstract

In this work, 1,2,3,4,5,8-hexahydro-1,3,7-trimethyl-2,4-dioxopyrido[2,3-d]pyrimidine-6-carboxamide derivatives were synthesized in a simple and efficient method from the four-component condensation reaction of diketene, an aliphatic or aromatic amine, an aromatic aldehyde, and 6-amino-1,3-dimethyluracil in the presence of a catalytic amount of p-toluenesulfonic acid under mild conditions at ambient temperature in high yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis
  • Aldehydes / chemistry*
  • Amines / chemical synthesis
  • Amines / chemistry*
  • Benzenesulfonates / chemical synthesis
  • Benzenesulfonates / chemistry
  • Combinatorial Chemistry Techniques / economics
  • Combinatorial Chemistry Techniques / methods*
  • Hydrocarbons, Acyclic / chemical synthesis
  • Hydrocarbons, Acyclic / chemistry
  • Hydrocarbons, Aromatic / chemical synthesis
  • Hydrocarbons, Aromatic / chemistry
  • Lactones / chemical synthesis
  • Lactones / chemistry*
  • Molecular Structure
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Small Molecule Libraries / chemical synthesis
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / economics
  • Uracil / analogs & derivatives*
  • Uracil / chemical synthesis
  • Uracil / chemistry

Substances

  • 1,2,3,4,5,8-hexahydro-1,3,7-trimethyl-2,4-dioxopyrido(2,3-d)pyrimidine-6-carboxamide
  • 6-amino-1,3-dimethyl uracil
  • Aldehydes
  • Amines
  • Benzenesulfonates
  • Hydrocarbons, Acyclic
  • Hydrocarbons, Aromatic
  • Lactones
  • Pyrimidines
  • Small Molecule Libraries
  • diketene
  • Uracil
  • 4-toluenesulfonic acid