Purines. XLVI. Preparation of 1-Ethyladenine from Adenosine

Tozo FUJII; Taisuke ITAYA; Fumiko TANAKA; Tohru SAITO; Hiromi HISATA

doi:10.1248/cpb.38.3463

Tozo FUJII, Taisuke ITAYA, Fumiko TANAKA, Tohru SAITO, Hiromi HISATA

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Keywords: adenosine, ethylation, 1-ethyladenosine, acid hydrolysis, glycosidic cleavage, 1-ethyladenine, UV, ^1H-NMR, acid dissociation constant

JOURNAL FREE ACCESS

1990 Volume 38 Issue 12 Pages 3463-3465

DOI https://doi.org/10.1248/cpb.38.3463

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Abstract

A detailed account is given of the synthesis and glycosidec cleavage of 1-ehyladenosine (2b), which established an alternative synthesis of 1-ethyladenine (3b). Ethylation of adenosine (1) with EtI in AcNMe₂ at 35-38°C for 90h gave 2b·HI in 54% yield. The hydriodide 2b·HI was readily converted into the perchlorate 2b·HClO₄ and into the free nucleoside 2b. Treatment of 2b·HI with 0.5N aqueous HCl at 92-94°C for 30min or that of 2b·HClO₄ with boiling AcOH for 60min produced the aglycone 3b in good yield. The free base easily formed the hydrochloride 3b·HCl, and the perchlorate 3b·HClO₄ as well.

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