Studies on Pyrimidine Derivatives. XXXVIII.1) Cross-Coupling Reaction of N-Heteroaryl Iodides with Ethoxycarbonylmethylzinc Bromide in the Presence of Palladium Catalyst

Hiroshi Yamanaka, Masayuki Annaka, Yoshinori Kondo, Takao Sakamoto

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

In the presence of tetrakis(triphenylphosphine)palladium, 2-iodo-4,6-dimethylpyrimidine and 4-iodo-2,6-dimethylpyrimidine reacted with ethoxycarbonylmethylzinc bromide (Reformatsky reagent) to give ethyl 4,6-dimethyl-2-pyrimidineacetate and ethyl 2,6-dimethyl-4-pyrimidineacetate, respectively. In contrast, the reaction of 5-iodo-2,4-dimethylpyrimidine with the same reagent resulted in recovery of the starting iodide. Similar results were observed in the reactions of various N-heteroaryl iodides.

Original languageEnglish
Pages (from-to)4309-4313
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume33
Issue number10
DOIs
Publication statusPublished - 1985 Jan 1

Keywords

  • N-hetero-arylacetic acid
  • N-heteroaryl halide
  • Reformatsky reagent
  • cross-coupling reaction
  • ethyl bromoacetate
  • palladium catalyst

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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