Methanol → 6-Amino-9-benzyl-2-(4-hydroxybutoxy)-8-methoxypurine

HRID 2269167Notes

Reaction equation

HRID 2269167 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-:25].[Na+].[CH3:27]O>>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:25][CH3:27])[N:6]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18332702HCID 18332702, compound

Product 1

HCID 183327246-Amino-9-benzyl-2-(4-hydroxybutoxy)-8-methoxypurineYield 68%

Procedure

To 6-amino-9-benzyl-8-bromo-2-(4-hydroxybutoxy)purine (185 mg, 0.472 mmol) in 10 ml of methanol was added 1N aqueous sodium hydroxide (40 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 (123 mg, yield 68%).

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-27f5bffe0ecf4c13af8fc457229d6ac2
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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