PALLADIUM-CATALYZED REACTION OF METHYL 5-AMINO-4-CHLORO-2-METHYLTHIOPYRROLO[2,3-d]PYRIMIDINE-6-CARBOXYLATE WITH ARYLBORONIC ACIDS. SYNTHESIS OF 1,3,4,6-TETRAAZADIBENZO[cd,f]AZULENE HETEROCYCLIC SYSTEM

Authors

  • J. Dodonova Vilnius University, Department of Organic Chemistry, Vilnius LT-03225
  • I. Uogintaite Vilnius University, Department of Organic Chemistry, Vilnius LT-03225
  • V. Masevicius Vilnius University, Department of Organic Chemistry, Vilnius LT-03225
  • S. Tumkevicius Vilnius University, Department of Organic Chemistry, Vilnius LT-03225

DOI:

https://doi.org/10.1007/5056

Keywords:

arylboronic acids, pyrrolo[2, 3-d]pyrimidines, 1, 3, 4, 6-tetraazadibenzo[cd, f]azulene, palladium catalysis, Suzuki–Miyaura reaction.

Abstract

Densely substituted methyl 5-amino-4-aryl-7-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylates were synthesized by the palladium-catalyzed cross-coupling reaction of methyl 5-amino-4-chloro-7-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimi-dine-6-carboxylate with arylboronic acids using Pd(OAc)2/dicyclohexyl(2-biphenyl)phosphine/K3PO4 as a catalyst system. Reaction of methyl 5-amino-4-chloro-7-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate with 2-formylphenylboronic acid led to a novel heterocyclic system – 1,3,4,6-tetraazadibenzo[cd,f]azulene.

How to Cite
Dodonova, J.; Uogintaite, I.; Masevicius, V.; Tumkevicius, S.  Chem. Heterocycl. Compd. 2010, 46, 1122. [Khim. Geterotsikl. Soedin. 2010, 1391.]

For this article in the English edition see DOI 10.1007/s10593-010-0636-5

 

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Published

2019-03-21

Issue

No. 9 (2010)

Section

Original Papers