Purines. LXXIX. Synthesis and hydrolysis of 3-methoxyadenine and its N6-benzyl derivative leading to the corresponding 2-hydroxyadenines

Article abstract of DOI:10.1248/cpb.47.554

Methylation of adenine 3-oxide (8a) with MeI in AcNMe₂ afforded 3- methoxyadenine (9a) in 44% yield. This compound (9a) underwent hydroxide-ion attack at the 2-position to give 2-hydroxyadenine (isoguanine) (10a) in 38% yield. A parallel reaction sequence starting from N⁶-benzyladenine 3-oxide (8c) and proceeding through N⁶-benzyl-3-methoxyadenine (9c) provided N⁶- benzyl-2-hydroxyadenine (10c) in 29% overall yield, together with a small amount of N⁶-benzyladenine (11c).

Full text of DOI:10.1248/cpb.47.554

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