Purines. II. An Alternative Synthesis of 1-Alkoxy-9-alkyladenine Salts

1971 Chemical and pharmaceutical bulletin  
Treatment of 9-alkyladenines (Ia, b, c) with 30% aqueous hydrogen peroxide in acetic yield. The 1-N-oxides were found to undergo alkylation almost exclusively at the oxygen atoms of the N-oxide groups when treated separately with methyl iodide, ethyl iodide, and benzyl bromide in N,N-dimethylacetamide at room temperature, and the corresponding salts (III) of all the nine possible 1-alkoxy-9-alkyladenines were obtained in excellent yields. 1-Ethoxyadenosine hydriodide and 1-benzyloxyadenosine
more » ... chlorate were also prepared from adenosine 1-oxide (II d) in a similar way. The ultraviolet and nuclear magnetic resonance spectral data on the 1-alkoxyadenine derivatives obtained in the previous and present studies are collected in Tables II and III. In connection with our recently published study 1, 5) of the alkylation of 1-alkoxyadenines (IV) leading to 1-alkoxy-9-alkyladenine salts (III), we were interested in investigating the site of alkylation of 9-alkyladenine 1-oxides (II) as well as adenosine 1-oxide (II d). This paper reports the details of our initial research in this area, which has been concerned with an alternative synthesis of III from 9-alkyladenines (I) through II. A number of the results described here have been recorded in a preliminary form. 6) Chart 1 Treatment of 9-methyladenine (I a) 1, 5) with 30% aqueous hydrogen peroxide in acetic 1-oxide (II b) and 9-benzyladenine 1-oxide (II c) were separately obtained from the corresponding 9-alkyladenines (I b, c) 1, 5) in 69-71% yield. The 1-N-oxide structure was assignable by
doi:10.1248/cpb.19.1368 fatcat:adepxf7yzngq5geg3cnoxl3p5y