1-Propanol → HCID 12898912, compound

HRID 2269104Notes

Reaction equation

HRID 2269104 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.[Na].[CH2:20]([OH:23])[CH2:21][CH3:22]>>[NH2:1][C:2]1[N:10]=[C:9]([O:23][CH2:20][CH2:21][CH3:22])[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 3

HCID 10311-PropanolHCID 2764829-Benzyl-2-chloro-9h-purin-6-amineHCID 5360545Sodium

Product 1

HCID 12898912HCID 12898912, compoundYield 74%

Procedure

6-Amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) and sodium propylate (316 mg, 3.85 mmol) were dissolved in 1-propanol (20 ml) and then the solution was refluxed on heating under stirring for 3 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 (162 mg, yield 74%).

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-3f73ccb005924e5d9e34442d10692180
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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