1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 178509051, compound

HRID 2269027Notes

Reaction equation

HRID 2269027 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+].[C:26]1(=[O:39])[N:30]([CH2:31][CH2:32]Br)[C:29](=[O:34])[C:28]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:27]12>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:32][CH2:31][N:30]2[C:26](=[O:39])[C:27]3=[CH:38][CH:37]=[CH:36][CH:35]=[C:28]3[C:29]2=[O:34])[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 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 178509051HCID 178509051, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Amino-9-benzyl-8-hydroxy-2-mercaptopurine (120 mg, 0.44 mmol) was suspended in dimethylformamide (10 ml). To the suspension were added potassium carbonate (60 mg, 0.43 mmol) and 2-phthalimidoethyl bromide (112 mg, 0.44 mmol) in order. The mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo and to the residue was added saturated brine. The mixture was extracted with ethyl acetate, the organic layer was dried on magnesium sulfate, and the solvent was removed in vacuo. Methanol was added to the residue, and the resulting crystals were taken by filtration to give the subject compound (107 mg, yield 54%).

Workup

  1. customThe solvent was removed in vacuo and to the residue
  2. additionwas added saturated brine
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe organic layer was dried on magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. additionMethanol was added to the residue
  7. filtrationthe resulting crystals were taken by filtration

Sources & evidence

ORD record
ord-2a21f11188f641fc80963968ea5808e7
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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