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- W2084647009 abstract "The chlorination of 6-trifluoromethyluracils by phosphorus oxychloride in the presence of N,N-dimethylaniline was studied and compared with results obtained with 6-methyluracils. 6-Trifluoromethyluracil and its 5-chloro analog afforded moderate yields of the di- and trichloropyrimidines, accompanied by good yields of the 2-N-methylanilino by-products, after a 3-hour reaction time. After 24 hours, the 2-N-methylanilinopyrimidines were the primary or sole products. A small yield of 2,4-bis(N-methylanilino)-6-trifluoromethylpyrimidine was also obtained. The 6-methyluracils afforded high yields of the di- and trichloropyrimidines, after 3 and 24 hours, along with minor amounts of the 2-N-methylanilino by-products. After 48 hours, the proportion of 2,4-dichloro-6-methylpyrimidine decreased, and the 2-N-methylanilino product increased. 2-Chloro-4-methylanilino-6-methylpyrimidine and bis(2-N-methylanilino)-6-methylpyrimidine were also formed in small amounts. The chlorination products from 5-chloro-6-methyluracil remained constant over 188 hours of reaction time. It appears that the π electron distribution around the ring, as influenced by the substituents, controls the course of the chlorination and by-product formation. Since the amination by a tertiary amine is a type of Hofmann reaction, the presence of the chlorine in the 5 position of the ring adds steric hindrance and thus enhances the regiospecificity of the formation of by-products." @default.
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- W2084647009 date "1984-07-01" @default.
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- W2084647009 title "Pyrimidines. 7. A study of the chlorination of pyrimidines with phosphorus oxychloride in the presence of<i>N,N</i>-dimethylaniline" @default.
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- W2084647009 doi "https://doi.org/10.1002/jhet.5570210447" @default.
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