Water → 2,6-Diamino-9-benzylpurine

HRID 2269111

Reaction equation

HRID 2269111 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([NH2:11])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 309762,6-Diaminopurine

Product 1

HCID 2389302,6-Diamino-9-benzylpurineYield 19.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Diaminopurine (5.00 g, 33.3 mmol) and potassium carbonate (6.91 g, 50.0 mmol) were suspended in DMF (250 ml). Benzyl bromide (8.55 g, 50 mmol) was added thereto and the mixture was stirred at room temperature for 5 hours. After condensing the reaction mixture in vacuo, to the residue was added water and the mixture was extracted with chloroform. The organic layer was dried on sodium sulfate, filtered and the solvent in the filtrate was evaporated in vacuo. The residue was purified with silica gel chromatography (5% methanol/chloroform) to give the subject compound (1.56 g, yield 19%).

Workup

  1. customAfter condensing the reaction mixture in vacuo
  2. extractionthe mixture was extracted with chloroform
  3. customThe organic layer was dried on sodium sulfate
  4. filtrationfiltered
  5. customthe solvent in the filtrate was evaporated in vacuo
  6. customThe residue was purified with silica gel chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-58b11c80c4e846ada5570567c693723c
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Linked notes

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