Acetic Acid → Diacetylguanine

HRID 265618Notes

Reaction equation

HRID 265618 reaction equation
[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[C:2]1[NH2:3].[C:12]([OH:15])(=O)[CH3:13].[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:16]([N:3]([C:12](=[O:15])[CH3:13])[C:2]1[NH:1][C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 135398634Guanine

Product 1

HCID 136360183DiacetylguanineYield 95%

Procedure

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.

Workup

  1. customif solvents are removed by distillation

Sources & evidence

ORD record
ord-81823c6002104188912a3c6eef0924b8
Source dataset
uspto-grants-1997_07
Patent number
US05648489

Reaction notes

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