ピリミジン誘導体(第6報)オロチン酸, ウラシル及びピリミド-[5,4-d]ピリミジン誘道体の合成研究

概要

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A new reaction was found by which 5-cholroorotic acid (III) was obtained via the intermediate (II) by the treatment of ethyl orotate (I) with pyridine and thionyl chloride, a nucleophilic reagent. Also, both 5-chlorouracil (V) and 5-chloromethylthiourail (VIII) were formed respectively by a similar reaction of uracil (IV) and methylthiouracil (VII). It is considered that this reaction is an electrophilic reaction with the complex of thionylpyridinium chloride, and that an electron releasing group at the 4-position tends to lower the yield of 5-chloro compound, while an electron-withdrawing group gives a higher yield of 5-chloro compound. The reaction of II or III with amine bases gave their substituted compounds, in which substituents at the 4- and 5-positions did not lie coplanar to the pyrimidine ring. Furthermore, it was found that the treatment of guanidine derivative (XIV) with cone. sulfuric acid afforded the amino form (XX) of pyrimido[5,4-d]pyrimidine derivative.
公益社団法人日本薬学会の論文
1972-07-25