Sodium Methoxide → HCID 18332727, compound

HRID 2269144Notes

Reaction equation

HRID 2269144 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH: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][O-:25].[Na+]>CO>[NH2:1][C:2]1[N:10]=[C:9]([NH: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 10942334Sodium MethoxideHCID 183326866-Amino-9-benzyl-8-bromo-2-(2-methoxyethyl)aminopurine

Product 1

HCID 18332727HCID 18332727, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Amino-9-benzyl-8-bromo-2-(2-methoxyethyl)aminopurine (68 mg, 0.18 mmol) was dissolved in 28% sodium methoxide in methanol (30 ml) and the solution was refluxed on heating under stirring for 4 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 and concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (26 mg, yield 44%).

Workup

  1. temperaturethe solution was refluxed
  2. temperatureon heating
  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. concentrationconcentrated in vacuo to dryness
  8. customThe residue was purified with silica gel chromatography (2% methanol/chloroform)

Sources & evidence

ORD record
ord-ea00bfe9a00345799fc6651ef93bd514
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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