Chloroacetonitrile → HCID 178511465, compound

HRID 2269055Notes

Reaction equation

HRID 2269055 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][C:28]#[N:29]>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:27][C:28]#[N:29])[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 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 178511465HCID 178511465, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 6-amino-9-benzyl-8-hydroxy-2-mercaptopurine (150 mg, 0.55 mmol) was suspended in dimethylformamide (10 ml). To the suspension were added potassium carbonate (81 mg, 0.59 mmol) and chloroacetonitrile (44 mg, 0.59 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 (1% ammonia, 5% methanol/chloroform) to give the subject compound (58 mg, yield 25%).

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 (1% ammonia, 5% methanol/chloroform)

Sources & evidence

ORD record
ord-20cae090fc814db8b8632ce0be006503
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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