High throughput synthesis of extended pyrazolo[3,4-d]dihydropyrimidines

ACS Comb Sci. 2012 Aug 13;14(8):465-70. doi: 10.1021/co300063x. Epub 2012 Jul 20.

Abstract

Thirteen 5-hetarylaminopyrazoles were synthesized in 62-93% yield through the arylation of 1-isopropyl- and 1-phenyl-5-aminopyrazoles with electrophilic hetarylhalides under optimized conditions. Condensation of 5-hetarylaminopyrazoles with carbonyl compounds facilitated by AcOH or Me(3)SiCl furnished 23 pyrazolo[3,4-d]dihydropyrimidines in 69-86% yield. The target compounds were isolated through simple crystallization. The scope and limitation of the method are discussed.

MeSH terms

  • Combinatorial Chemistry Techniques
  • Molecular Structure
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry

Substances

  • Pyrazoles
  • Pyrimidines