Abstract
Treatment of 1-methoxy-9-methyladenine hydriodide (Ia) with hot pyridine has been found to produce 1-methylpyridinium salt (IIf) and 9-methyladenine 1-oxide (IIIf). Similarly, pyridine was ethylated with 1-ethoxy-9-benzyladenine hydriodide (Ic) to give 1-ethylpyridinium iodide (IIg : X=I) and 9-benzyladenine 1-oxide (IIIh). Benzyl alcohol was possible to be methylated with 1-methoxy-9-benzyladenine hydriodide (Ib), although yield of benzyl methyl ether was poor. Reactions of 1-benzyloxy-9-benzyladenine hydrobromide (Id) with various nucleophiles such as pyridine, aniline, C2H5S-, CH3CO2-, ethanol, and water also proceeded smoothly and yielded the corresponding benzylated products and IIIh in good yields. Benzylation of adenine with Id in N, N-dimethylacetamide at 35° furnished 3-benzyl-adenine as the major product and 9-benzyladenine and 1-benzyladenine as the minor products. The reactivities of Id toward pyridine and ethanol have been compared with those of 1-benzyloxy-9-benzyladenine perchlorate (Ie), and possible mechanisms of the alkylation with 1-alkoxyadenine derivatives (type I) are discussed.
