Methyl iodide → HCID 178503491, compound

HRID 2269067Notes

Reaction equation

HRID 2269067 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:20])[N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI>CO>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH3:21])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:20])[N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178509060HCID 178509060, compound

Product 1

HCID 178503491HCID 178503491, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-amino-9-(4-fluorobenzyl)-8-hydroxy-2-mercaptopurine (200 mg, 0.687 mmol) was suspended in methanol (20 ml). To the suspension were added potassium carbonate (190 mg, 1.37 mmol) and methyl iodide (975 mg, 6.87 mmol) in order. The mixture was stirred at room temperature for 30 minutes. The reaction mixture were evaporated in vacuo to dryness and extracted with chloroform. The organic layer was dried on sodium sulfate. After removal of the solvent in vacuo, the residue was purified by silica gel chromatography (3% methanol/chloroform) to give the subject compound (63 mg, yield 30%).

Workup

  1. customThe reaction mixture were evaporated in vacuo to dryness
  2. extractionextracted with chloroform
  3. customThe organic layer was dried on sodium sulfate
  4. customAfter removal of the solvent in vacuo
  5. customthe residue was purified by silica gel chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-637e0c00fb0d4ea4a28013bdee4f2204
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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