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Synthesis of 2,4-disubstituted 6-phenyl-7H-pyrrolo[3,2-d]-pyrimidin-7-one 5-oxides

✍ Scribed by Inga Cikotiene; Erika Pudziuvelyte; Algirdas Brukstus

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
256 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A relatively short and efficient method for the utilization of 4,6‐dichloro‐2‐methylthio‐5‐nitropyrimidine (1) in the synthesis of the poly substituted pyrrolo[3,2‐d]pyrimidin‐7‐one 5‐oxides (6a‐g) is reported. Some new 4‐substituted 6‐chloro‐2‐methylthio‐5‐nitropyrimidines (2a‐e) were prepared by reaction of 4,6‐dichloro‐2‐methylthio‐5‐nitropyrimidine (1) with amines. 4‐Substituted 2‐methylthio‐5‐nitro‐6‐phenylethynylpyrimidines (3a‐e), obtained from 4‐substituted 6‐chloro‐2‐methylthio‐5‐nitropyrimidines (2a‐e) via palladium‐catalyzed Sonagashira coupling reaction with 1‐phenylacetylene, underwent smooth cyclization reaction in boiling 2‐propanol in the presence of catalytic amount of pyridine to give 4‐substituted 2‐methylthio‐6‐phenyl‐7__H__‐pyrrolo[3,2‐d]pyrimidin‐7‐one 5‐oxides (4a‐e). The methylthio group of the latter compounds can be easily and selectively oxidized by m‐chloroperbenzoic acid and replaced with different amines.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of 2-Chlo
ChemInform Abstract: Synthesis of 2-Chloro-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one.
✍ Mui Cheung; Philip A. Harris; Karen E. Lackey 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB 👁 1 views

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