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Pyrimidones. 2 . Synthesis and reactions of 2‐chloropyrimidines
Author(s) -
Coppola Gary M.,
Hardtmann Goetz E.,
Huegi Bruno S.
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170724
Subject(s) - chemistry , phosphorus pentachloride , phenyllithium , alkylation , nucleophile , alkyl , hydrazine (antidepressant) , aryl , triethyl orthoformate , pyrimidine , organic chemistry , ring (chemistry) , phosphorus , sulfur , oxidizing agent , nitrogen , carbon disulfide , medicinal chemistry , stereochemistry , catalysis , chromatography
The treatment of 1‐alkyl‐5‐aryl and 1‐alkyl‐4,5‐diaryl‐2‐(1 H )pyrimidones with phosphorus oxychloride and phosphorus pentachloride resulted in chlorination and dealkylation to furnish 2‐chloro‐5‐aryl (or 4,5‐diaryl)‐pyrimidines. These chlorpyrimidines were reacted with a variety of nitrogen, oxygen, sulfur, and carbon nucleophiles to produce the corresponding 2‐substituted pyrimidines. In the case of phenyllithium, attack occurred at the 4‐position of the pyrimidine ring yielding 11 . Triazolopyrimidine 9 was synthesized via the treatment of 2d with hydrazine followed by reaction with triethyl orthoformate.