Purines. LXXIX. Synthesis and Hydrolysis of 3-Methoxyadenine and Its N6-Benzyl Derivative Leading to the Corresponding 2-Hydroxyadenines

Taisuke ITAYA; Tae KANAI; Yasutaka TAKADA; Miki KANEKO; Kensuke YASUHARA; Tozo FUJII

doi:10.1248/cpb.47.554

Purines. LXXIX. Synthesis and Hydrolysis of 3-Methoxyadenine and Its N⁶-Benzyl Derivative Leading to the Corresponding 2-Hydroxyadenines

Taisuke ITAYA, Tae KANAI, Yasutaka TAKADA, Miki KANEKO, Kensuke YASUHARA, Tozo FUJII

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Keywords: adenine 3-oxide methylation, 3-methoxyadenine hydrolysis, isoguanine synthesis, N⁶-benzyl-3-methoxyadenine hydrolysis

JOURNAL FREE ACCESS

1999 Volume 47 Issue 4 Pages 554-556

DOI https://doi.org/10.1248/cpb.47.554

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Abstract

Methylation of adenine 3-oxide (8a) with MeI in AcNMe₂ afforded 3-emthoxyadenine (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).

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