Synthesis and substitution reactions of 4(6)-chlorodihydropyrimidines

Hidetsura Cho, Yoshizumi Yasui, Satoshi Kobayashi, Eunsang Kwon, Mieko Arisawa, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Chlorination of the corresponding ketones with phenylphosphonic dichloride (PhPOCl2) provided ethyl 6(4)-chloro-2-methyl-4(6)-phenyl-1,4(6)- dihydropyrimidine-5-carboxylate in good yield. The cross-coupling reactions of organoboronic acids or triethylborane with 1-tert-butyl 5-ethyl 4-chloro-2- methyl-6-phenyl-1,6-dihydropyrimidine-1,5-dicarboxylate synthesized by regiospecific alkoxycarbonylation of the chlorinated dihydropyrimidine afforded 1,4(3,4)-dihydropyrimidines having a variety of functional groups at position-6(4) in good to excellent yields.

Original languageEnglish
Pages (from-to)1807-1818
Number of pages12
JournalHeterocycles
Volume83
Issue number8
DOIs
Publication statusPublished - 2011 Aug 10

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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