3-Chloropropionitrile → HCID 178511214, compound

HRID 2269054Notes

Reaction equation

HRID 2269054 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([SH:11])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:19])[N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:27][CH2:28][C:29]#[N:30]>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:27][CH2:28][C:29]#[N:30])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:19])[N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 109633-ChloropropionitrileHCID 11430Potassium CarbonateHCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 178511214HCID 178511214, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 6-amino-9-benzyl-8-hydroxy-2-mercaptopurine (134 mg, 0.49 mmol) was suspended in dimethylformamide (60 ml). To the suspension were added potassium carbonate (100 mg, 0.72 mmol) and 3-chloropropionitrile (65 mg, 0.73 mmol) in order. The mixture was stirred at room temperature for 3 hours. The solvent was removed in vacuo, 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 in vacuo, the residue was purified by silica gel chromatography (5% methanol/chloroform) to give the subject compound (72 mg, yield 45%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionto the residue was added water
  3. extractionThe mixture was extracted with chloroform
  4. customthe organic layer was dried on sodium sulfate
  5. customAfter removal of the solvent in vacuo
  6. customthe residue was purified by silica gel chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-4688a4a6ed194aa48ab35727549ce923
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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