9-Benzyl-2-chloro-9h-purin-6-amine → HCID 18332810, compound

HRID 2269103Notes

Reaction equation

HRID 2269103 reaction equation
[NH2:1][C:2]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:19][CH2:20][O-:21].[Na+]>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]([O:21][CH2:20][CH3:19])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 2764829-Benzyl-2-chloro-9h-purin-6-amineHCID 2723922Sodium ethoxide

Product 1

HCID 18332810HCID 18332810, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) and sodium ethylate (262 mg, 3.85 mmol) were dissolved in ethanol (20 ml) and then the solution was refluxed on heating under stirring for 20 hours. The reaction mixture was evaporated 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 evaporated in vacuo to dryness. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (151 mg, yield 73%).

Workup

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

Sources & evidence

ORD record
ord-b4371892ff8e4f1eb26a728fcca699a3
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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