Methanol → 6-Amino-9-benzyl-2-(3-ethoxypropoxy)-8-methoxypurine

HRID 2269165Notes

Reaction equation

HRID 2269165 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH3:17])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-:26].[Na+].[CH3:28]O>>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH3:17])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:26][CH3:28])[N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 183327126-Amino-9-benzyl-8-bromo-2-(3-ethoxypropoxy)purine

Product 1

HCID 183327296-Amino-9-benzyl-2-(3-ethoxypropoxy)-8-methoxypurineYield 85%

Procedure

To 6-amino-9-benzyl-8-bromo-2-(3-ethoxypropoxy)purine (250 mg, 0.36 mmol) in 20 ml of methanol was added 1N aqueous sodium hydroxide (80 ml). The mixture was refluxed on heating under stirring for 2 hours. The reaction mixture was concentrated in vacuo to dryness. To the residue was added water and the mixture was extracted with chloroform. The organic layer was dried on sodium sulfate and the solvent was removed. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (187 mg, yield 85%).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureon heating
  3. concentrationThe reaction mixture was concentrated in vacuo to dryness
  4. additionTo the residue was added water
  5. extractionthe mixture was extracted with chloroform
  6. customThe organic layer was dried on sodium sulfate
  7. customthe solvent was removed
  8. customThe residue was purified with silica gel chromatography (2% methanol/chloroform)

Sources & evidence

ORD record
ord-0f1268877f4d488ebab15805c66fa8be
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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