Acetic Anhydride → N2-acetyl-7-benzylguanine

HRID 1069392Notes

Reaction equation

HRID 1069392 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.Cl.Cl.[CH2:10]([N:17]1[C:25]2[C:24](=[O:26])[NH:23][C:22]([NH2:27])=[N:21][C:20]=2[N:19]=[CH:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])O.[Na+].[OH-].[Na+]>C(O)(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:24]([NH:23][C:22]1[NH:27][C:5](=[O:7])[C:6]2[N:17]([CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:18]=[N:19][C:20]=2[N:21]=1)(=[O:26])[CH3:25]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 1358103037-Benzylguanine Dihydrochloride

Product 1

HCID 135471186N2-acetyl-7-benzylguanineYield 95.7%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Acetic anhydride (4.44 ml, 45.1 mmols) and 132.8 mg (0.598 mmols) of p-toluenesulfonic acid monohydrate were added to a solution of 4.37 g (13.9 mmols) of 7-benzylguanine dihydrochloride in 9 ml of acetic acid. The mixture was reacted at 105° C. for 3 hours, and then allowed to cool. Water (180 ml) was poured into the reaction solution, and 150 ml of a 5-% sodium hydrogencarbonate aqueous solution and 100 ml of a 1−N sodium hydroxide aqueous solution were added thereto to adjust the pH to 5.3. Crystals were filtered, washed with 50 ml of water, and then dried at 55° C. for 5 hours under reduced pressure to obtain 3.77 g (13.3 mmols) of N2-acetyl-7-benzylguanine as a white solid in a yield of 95.7%.

Workup

  1. customThe mixture was reacted at 105° C. for 3 hours
  2. temperatureto cool
  3. additionwere added
  4. filtrationCrystals were filtered
  5. washwashed with 50 ml of water
  6. customdried at 55° C. for 5 hours under reduced pressure

Sources & evidence

ORD record
ord-62aa11c678a740f5b87bbc161affe5c5
Source dataset
uspto-grants-2001_06
Patent number
US06252075B1

Reaction notes

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