Studies on Pyrimidine Derivatives. XXVIII. Synthesis of Pyridopyrimidine Derivatives by Cross-coupling of Halopyrimidines with Olefins and Acetylenes

Takao Sakamoto, Yoshinori Kondo, Hiroshi Yamanaka

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Three kinds of pyridopyrimidines were synthesized from appropriate pyrimidine derivatives. Cross-coupling of 4-amino-5-iodopyrimidines with α,β-unsaturated carboxylic esters followed by ring-closure afforded pyrido[2,3-d]pyrimidines. Ammonolysis of 4-ethoxycarbonyl-5-phenylethynyl- and 5-ethoxycarbonyl-4-phenylethynyl-pyrimidines which were obtained by cross-coupling of the corresponding halopyrimidines with phenylacetylene, gave pyrido[3,4-d]- and pyrido[4,3-d]-pyrimidines, respectively.

Original languageEnglish
Pages (from-to)2410-2416
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Volume30
Issue number7
DOIs
Publication statusPublished - 1982 Jan 1

Keywords

  • 5-iodopyrimidine
  • ethyl 5-pyrimidineacrylate
  • palladium-catalyzed cross-coupling reaction
  • phenylethynylpyrimidine
  • pyridopyrimidine
  • ring-closure reaction
  • styrylpyrimidine

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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