Methanol → HCID 11130326, compound

HRID 2269140Notes

Reaction equation

HRID 2269140 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH3:13])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-:22].[Na+].[CH3:24]O>>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH3:13])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:22][CH3:24])[N:6]2[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11782995HCID 11782995, compound

Product 1

HCID 11130326HCID 11130326, compoundYield 73%

Procedure

To 6-amino-9-benzyl-8-bromo-2-ethoxypurine (35 mg, 0.101 mmol) in 5 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 (22 mg, yield 73%).

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-f6f34bf446cf423381346187a8bb8a98
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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