1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → 6-Amino-9-benzyl-8-hydroxy-2-(3-phthalimidopropylthio)purine

HRID 2269028Notes

Reaction equation

HRID 2269028 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:20](=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][CH2:20][CH2:32][CH2:31][N:30]2[C:29](=[O:34])[C:28]3=[CH:35][CH:36]=[CH:37][CH:38]=[C:27]3[C:26]2=[O:39])[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 1785090456-Amino-9-benzyl-8-hydroxy-2-(3-phthalimidopropylthio)purineYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Amino-9-benzyl-8-hydroxy-2-mercaptopurine (110 mg, 0.40 mmol) was suspended in dimethylformamide (10 ml). To the suspension were added potassium carbonate (50 mg, 0.40 mmol) and 2-phthalimidoethyl bromide (108 mg, 0.40 mmol) in order. The mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo, water and methanol were added to the residue, and the resulting crystals were taken by filtration to give the subject compound (138 mg, yield 75%).

Workup

  1. customThe solvent was removed in vacuo, water and methanol
  2. additionwere added to the residue
  3. filtrationthe resulting crystals were taken by filtration

Sources & evidence

ORD record
ord-5f1899c1cbe748bbb5bed8fd6977008e
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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