Intermediates in the synthesis of purines and pteridines: selective hydrolysis of chloropyrimidines
Kazimierczuk, Z.; Lipski, M.; Shugar, D.
Acta Biochimica Polonica 19(4): 359-366
1972
ISSN/ISBN: 0001-527X PMID: 4664351 Document Number: 5430
1. Alkaline hydrolysis of 2,4,6-trichloropyrimidine at room temperature leads to 4,6-dichloro-2-hydroxypyrimidine, which may be isolated on a preparative scale in good yield. At higher temperatures, the final product is 6-chlorouracil. The latter may be more readily obtained by acid hydrolysis at room temperature of 4,6-dichloro2-hydroxypyrimidine. 2. Alkaline hydrolysis of 2,4-dichloropyrimidine to uracil has been shown to proceed via 4-chloro-2-hydroxypyrimidine, which may be isolated on a preparative scale in crude form. 3. The foregoing product may be converted directly to 4-alkoxy-2-hydroxypyrimidines, providing a simpler route to these useful derivatives than alkaline hydrolysis of 2,4-dialkoxypyrimidines. 4. Both 4-chloro-2-hydroxypyrimidine and 4,6-dichloro-2-hydroxypyrimidine are acid labile. Their ti ½ values for conversion to uracil and 6-chlorouracil at pH 1 and room temperature are, respectively, 26 and 31 min. 5. Some applications of the foregoing derivatives in various syntheses are described.
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