Parallel synthesis of 7-heteroaryl-pyrazolo[1,5-a]pyrimidine-3-carboxamides

Mol Divers. 2013 Nov;17(4):731-43. doi: 10.1007/s11030-013-9469-3. Epub 2013 Aug 22.

Abstract

A simple and practical four-step protocol for the parallel synthesis of 7-heteroaryl-pyrazolo[1,5-[Formula: see text]]pyrimidine-3-carboxamides was developed. The synthesis starts with transformation of commercially available 2-acetylpyridine and acetylpyrazine with [Formula: see text] [Formula: see text]-dimethylformamide dimethylacetal into the corresponding [Formula: see text]-3-(dimethylamino)-1-(heteroaryl)prop-2-en-1-ones followed by cyclisation with methyl 5-amino-1[Formula: see text]-pyrazole-4-carboxylate to give methyl 7-heteroarylpyrazolo[1,5-[Formula: see text]]pyrimidine-3-carboxylates. Hydrolysis of the ester group and subsequent amidation of the so formed carboxylic acids with 12 primary and secondary aliphatic amines furnished a library of 24 title compounds in good overall yields and purity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques*
  • Cyclization
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry

Substances

  • Pyrazoles
  • Pyrimidines
  • pyrazole
  • pyrimidine