Reactions of certain purin-8-ols with phosphorus oxychloride in the presence of N,N-diethylaniline Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/zk51vk912

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  • The reaction of certain purin-8-ols with phosphorus oxychloride and N,N-diethylaniline are described. 9-Amino-6-chloropurin-8-ol monohydrate reacted with phosphorus oxychloride and N, N-diethylaniline to yield the phosphorus oxychloride adduct. Other purin-8-ols were prepared and the production of analogs similar to the previously mentioned adduct was attempted. 6-Chloropurin-8-ol and 6, 9-diaminopurin-8-ol hydrochloride monohydrate reacted with phosphorus oxychloride and N, N-diethylaniline to yield water-soluble intermediates which could not be isolated. 6-Aminopurin-8-ol chlorinated in the 8-position in the presence of the reaction mixture rather than producing the phosphorus oxychloride adduct. In the course of the work described herein, two previously unreported compounds, 4-amino-6-hydrazino-5-nitropyrimidine and 6, 9-diaminopurin-8-ol hydrochloride monohydrate, were synthesized. Spectral data for these compounds are reported.
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