Methanol → 6-Amino-9-benzyl-8-methoxy-2-(2-methoxyethoxy)purine

HRID 2269170Notes

Reaction equation

HRID 2269170 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[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][O:14][CH3:15])[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 112789046-Amino-9-benzyl-8-methoxy-2-(2-methoxyethoxy)purineYield 43%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

6-Amino-9-benzyl-8-bromo-2-(2-methoxyethoxy)purine (69 mg, 0.18 mmol) in methanol (50 ml) was dissolved in 28% sodium methoxide/methanol (1 ml) and the mixture was refluxed on heating under stirring for 5 hours. The reaction mixture was concentrated in vacuo to dryness, and to the residue was added water. The solution was extracted with chloroform and the organic layer was dried on sodium sulfate and concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (3% methanol/chloroform) to give the subject compound (26 mg, yield 43%).

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 solution was extracted with chloroform
  6. customthe organic layer was dried on sodium sulfate
  7. concentrationconcentrated in vacuo to dryness
  8. customThe residue was purified with silica gel chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-e60485f01a9e4a7595c0c8fbedbd0975
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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