Potassium Carbonate → HCID 178467874, compound

HRID 2269062Notes

Reaction equation

HRID 2269062 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+].C1(C)C=CC(S(OC[CH:37]([O:39][CH2:40][CH3:41])[CH3:38])(=O)=O)=CC=1>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:20][CH2:41][CH2:40][O:39][CH2:37][CH3:38])[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 13955194HCID 13955194, compoundHCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 178467874HCID 178467874, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 6-amino-9-benzyl-8-hydroxy-2-mercaptopurine (80 mg, 0.65 mmol) was suspended in dimethylformamide (60 ml). To the suspension were added potassium carbonate (150 mg, 1.1 mmol) and 2-ethoxypropyl p-toluenesulfonate (280 mg, 1.1 mmol) in order. The mixture was stirred at room temperature for 4 hours. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (5% methanol/chloroform) to give the subject compound (69 mg, yield 30%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-e4df0dfd60ac457ab10c108cad51b8b2
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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