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

HRID 2269159Notes

Reaction equation

HRID 2269159 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14]C)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:24][OH:25]>C[O-].[Na+].CO>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][OH:14])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:25][CH3:24])[N:6]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 183327586-Amino-9-benzyl-8-bromo-2-(2-methoxyethoxy)purine

Product 1

HCID 183327336-Amino-9-benzyl-2-(2-hydroxyethoxy)-8-methoxypurineYield 69%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

6-Amino-9-benzyl-8-bromo-2-(2-methoxyethoxyl)purine (130 mg, 0.36 mmol) in methanol (50 ml) was dissolved in 28% sodium methoxide/methanol (3 ml) and the solution was refluxed on heating under stirring for 10 hours. The reaction mixture was concentrated in vacuo to dryness, and to the residue was added saturated brine. The mixture was extracted with chloroform and the organic layer was dried on sodium sulfate, followed by removal of the solvent. The residue was purified with silica gel chromatography (3% methanol/chloroform) to give the subject compound (78 mg, yield 69%).

Workup

  1. temperaturethe solution was refluxed
  2. temperatureon heating
  3. concentrationThe reaction mixture was concentrated in vacuo to dryness
  4. additionto the residue was added saturated brine
  5. extractionThe mixture was extracted with chloroform
  6. customthe organic layer was dried on sodium sulfate
  7. customfollowed by removal of the solvent
  8. customThe residue was purified with silica gel chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-c557cfc83efc4b45ba7a5ad916f3f933
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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