81281-47-2Relevant articles and documents
A FACILE CONVERSION OF THE 1-METHYL GROUP TO THE 1-AMINO GROUP OF XANTHINE DERIVATIVES
Ueda, Taisei,Oda, Noriichi,Sakakibara, Jinsaku,Takeya, Kazumi
, p. 2291 - 2294 (2007/10/02)
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 40percent 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 28-42percent yield.Deamination of these 7-substituted 1-amino-3-methylxanthines (IIa-b, IId-f) gave the corresponding theobromine derivatives (IVa-b, IVd-f) in 90-96percent yield.