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Communication | Regular issue | Vol 24, No. 9, 1986, pp.2449-2454
Published online, 1st January, 1970
DOI: 10.3987/R-1986-09-2449
■ A New Synthetic Route to 2-Deuterioadenines Substituted or Unsabustituted at the 9-Position

Tozo Fujii,* Tohru Saito, Kyoko Kizu, Hiromi Hayashibara, Yukinari Kumazawa, and Satoshi Nakajima

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

Abstract

9-Alkyl-2-deuterioadenines (VIIIb-d) , adenosine-2-d (VIIIe), and 2’-deoxyadenosine-2-d (VIIIf) were synthesized from the 9-substituted adenines Ib-f through cyclization of the monocyclic intermediates VIb-f with formic acid-d2 or 1-(formyl-d)-2(1H)-pyridone. Hydrolysis of VIIIe, prepared through this synthetic route, with 0.5 N aqueous HCl (reflux, 2 h) gave adenine-2-d (VIIIa) in 77% yield. Unambiguous assignments of the purine ring protons in the nmr spectra of the unlabeled adenines Ia-f have been made by comparison with those of the labeled adenines VIlla-f.