Methanol → 6-Amino-9-benzyl-8-methoxy-2-propoxypurine

HRID 2269141Notes

Reaction equation

HRID 2269141 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH3:14])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-:23].[Na+].[CH3:25]O>>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH3:14])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:23][CH3:25])[N:6]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11078946HCID 11078946, compound

Product 1

HCID 108815416-Amino-9-benzyl-8-methoxy-2-propoxypurineYield 93%

Procedure

To 6-amino-9-benzyl-8-bromo-2-propoxypurine (123 mg, 0.339 mmol) in 10 ml of methanol was added 10N aqueous sodium hydroxide (50 ml) and the solution was refluxed under heating for 2 hours. The reaction mixture was concentrated in vacuo to dryness and to the residue was added water. The mixture was extracted with chloroform and the organic layer was dried on sodium sulfate. After removal of the solvent the residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (99 mg, yield 93%).

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heating for 2 hours
  3. concentrationThe reaction mixture was concentrated in vacuo to dryness and to the residue
  4. additionwas added water
  5. extractionThe mixture was extracted with chloroform
  6. customthe organic layer was dried on sodium sulfate
  7. customAfter removal of the solvent the residue
  8. customwas purified with silica gel chromatography (1% methanol/chloroform)

Sources & evidence

ORD record
ord-7ebb03bef3264351b205320a5d72c0f0
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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