Potassium Carbonate → 6-Amino-9-benzyl-8-hydroxy-2-{[2-(2-ethoxyethoxy)ethyl]thio}purine

HRID 2269061Notes

Reaction equation

HRID 2269061 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+].[CH2:26]([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33]Br)[CH3:27]>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:27][CH2:26][O:28][CH2:29][CH2:30][O:31][CH2:32][CH3:33])[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 11430Potassium CarbonateHCID 70153241-Bromo-2-(2-ethoxyethoxy)ethaneHCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 1784680296-Amino-9-benzyl-8-hydroxy-2-{[2-(2-ethoxyethoxy)ethyl]thio}purineYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 6-amino-9-benzyl-8-hydroxy-2-mercaptopurine (470 mg, 1.7 mmol) was suspended in dimethylformamide (100 ml). To the suspension were added potassium carbonate (350 mg, 2.5 mmol) and 1-ethoxy-2-(2-bromoethoxy)ethane (505 mg, 2.6 mmol) in order. The mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (1% methanol/chloroform) to give the subject compound (147 mg, yield 22%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography (1% methanol/chloroform)

Sources & evidence

ORD record
ord-85834d791a3c47abbf0142ea45eb15fc
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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