Chloromethyl Methyl Ether → HCID 178502589, compound

HRID 2269033Notes

Reaction equation

HRID 2269033 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+].[CH3:26][O:27][CH2:28]Cl>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:26][O:27][CH3:28])[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 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 178502589HCID 178502589, compoundYield 69%

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 (65 ml). To the suspension were added potassium carbonate (100 mg, 0.72 mmol) and chloromethyl methyl ether (0.056 ml, 0.73 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 (2% methanol/chloroform) to give the subject compound (107 mg, yield 69%).

Workup

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

Sources & evidence

ORD record
ord-89eccd73a2bc4a69809af2d400677d72
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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