Pyrimidones. 2. Synthesis and reactions of 2‐chloropyrimidines

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Abstract
The treatment of 1‐alkyl‐5‐aryl and 1‐alkyl‐4,5‐diaryl‐2‐(1H)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.

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