Acetic Acid → Diacetylguanine

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Guanine has also been acetylated in acetic anhydride and acetic acid to give different products depending on the workup conditions. H. Matsumoto. et al. Chem.Pharm.Bull. 1988, 36 (3), 1153. For example, after the reaction mixture becomes an almost clear solution, if solvents are removed by distillation, only diacetyl guanine is obtained in 95% yield. However, the addition of water at 60° C. followed by stirring at room temperature overnight produces N2 -acetylguanine in 94.4% yield. If the reaction mixture is merely cooled down, a mixture of mono- and di-acetylguanine is produced.

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