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Communication | Regular issue | Vol 14, No. 11, 1980, pp.1729-1734
Published online, 1st January, 1970
DOI: 10.3987/R-1980-11-1729
Synthesis and Sodium Borohydride Reduction of 3,9-Dimethyladenine Perchlorate Deuterated at the 2-Position

Tozo Fujii,* Tohru Saito, Tsuyoshi Nakasaka, and Kyoko Kizu

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

Abstract

The NaBH4 reduction of 3,9-dimethyladenine perchlorate (Ib) in MeOH was found to give the 1,2-dihydro derivative III. The structure of III was confirmed by a similar reduction of the 2-deuterated isomer XIV, which was synthesized from the methylaminoimidazole VI through the deuteroformamido derivatives VIII and XI. 3-Benzyl-9-methyladenine-2-d perchlorate (XV) was similarly prepared from the N-benzylformamidoimidazole V through the deformylated derivative VII and the deuteroformamido derivatives IX and XII. Comparison of the nmr spectra of Ib and 3-benzyl-9-methyladenine perchlorate (Ie) with those of XIV and XV permitted a distinction between C(2)- and C(8)-proton signals observed for 3,9-dialkyladenine salts (Ia-1); the C(2)-proton resonates at lower field than does the C(8)-proton.