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Communication | Regular issue | Vol 16, No. 6, 1981, pp.909-913
Published online, 1st January, 1970
DOI: 10.3987/R-1981-06-0909
7,9-Dialkyladeninium Salts. An Alternative Synthesis, Ring Opening, and Rearrangement to N6,7-Dialkyladenines

Tozo Fujii,* Tohru Saito, and Isao Inoue

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


Alkylation of N’-alkoxy-1-alkyl-5-formamidoimidazole-4-carboxamidine (type I or II) (in the absence of any base) followed by hydrogenolysis of the N’-alkoxy group and cyclization (or vice versa) yielded the corresponding 7,9-dialkyladeninium salts (type VII), which readily rearranged to N6,7-dialkyladenines (type X) in boiling 1 N NaOH. Under milder basic conditions, VII underwent hydrolysis to produce 4-alkylamino-6-amino-5-formamidopyrimidines (VIII). The NaBH4 reduction of 7,9-dimethyladeninium iodide (VIIa, X = I) gave the 7,8-dihydro derivative (XI).