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Communication | Regular issue | Vol 19, No. 12, 1982, pp.2291-2294
Published online, 1st January, 1970
DOI: 10.3987/R-1982-12-2291
A Facile Conversion of the 1-Methyl Group to the 1-Amino Group of Xanthine Derivatives

Taisei Ueda, Noriichi Oda, Jinsaku Sakakibara, and Kazumi Takeya

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan


A facile conversion of the 1-methyl group to the 1-amino group of caffeine and its analogues was carried out by the reaction with hydrazine hydrate: Refluxing of caffeine(Ia) with a large amount of hydrazine hydrate (30 eq. mole) without any other solvents gave 1-amino-3,7-dimethylxanthine(IIa) in 40% yield. Similarly the reaction of 7-substituted 1,3-dimethylxanthines(Ib,Id-f) with hydrazine hydrate gave 7-substituted 1-amino-3-methylxanthines(IIb,IId-f) in 28-42% yield. Deamination of these 7-substituted 1-amino-3-methylxanthines (IIa-b, IId-f) gave the corresponding theobromine derivatives (IVa-b,IVd-f) in 90-96% yield.