Phosphoric Acid → Diacetylguanine

HRID 1080876Notes

Reaction equation

HRID 1080876 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH:8]1[C:17](=[O:18])[C:16]2[NH:15][CH:14]=[N:13][C:12]=2[N:11]=[C:9]1[NH2:10].P(=O)(O)(O)O.[CH3:24][C:25](OC(C)=O)=[O:26].CC(O)=O.N1C(=O)C2NC=NC=2N=C1N.OP(O)(O)=O>C(O)(=O)C>[C:25]([N:10]([C:5](=[O:7])[CH3:6])[C:9]1[NH:8][C:17](=[O:18])[C:16]2[NH:15][CH:14]=[N:13][C:12]=2[N:11]=1)(=[O:26])[CH3:24]

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 135398634Guanine2×HCID 136333567Ac2O AcOH guanine H3PO4

Product 1

HCID 136360183DiacetylguanineYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The effect of the ratio of acetic anhydride and acetic acid on the reaction time and yield was also studied. In general, any range of acetic anhydride, acetic acid, guanine and phosphoric acid can be used that provides the desired results. In the present work, it was found that a ratio of 15/10/1/0.05 (ml) of Ac2O/AcOH/guanine/H3PO4 is preferred. It was discovered that guanine could be acetylated using this ratio of reactants at reflux for 15 hours to give diacetylguanine with minimal discoloration in approximately 94% yield.

Workup

  1. customthat provides the
  2. customdesired results
  3. temperatureat reflux for 15 hours

Sources & evidence

ORD record
ord-976c28d10c8840548e254ab29039ac45
Source dataset
uspto-grants-1996_12
Patent number
US05583225

Reaction notes

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