Potassium Carbonate → HCID 178509037, compound

HRID 2269048Notes

Reaction equation

HRID 2269048 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+].[CH:26]1([CH2:32]Br)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:32][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[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 137636Cyclohexane, (bromomethyl)-HCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 178509037HCID 178509037, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 6-amino-9-benzyl-8-hydroxy-2-mercaptopurine (134 mg, 0.49 mmol) was suspended in dimethylformamide (60 ml). To the suspension were added potassium carbonate (100 mg, 0.72 mmol) and cyclohexylmethyl bromide (0.1 ml, 0.7 mmol) in order. The mixture was stirred at room temperature for 9 hours. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (3% methanol/chloroform) to give the subject compound (93 mg, yield 51%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-382930e8941845a4b097d4a5d35f76ec
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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