Methyl iodide → HCID 54139417, compound

HRID 1835731Notes

Reaction equation

HRID 1835731 reaction equation
[OH:1][C@H:2]([CH3:24])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][O:19][CH2:20][CH3:21])[C:13]([SH:22])=[N:12][C:11]=2[N:10]([CH3:23])[C:8]1=[O:9].[C:25](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[CH2:20]([O:19][CH2:18][N:14]1[C:15]2[C:16](=[O:17])[N:7]([CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]([OH:1])[CH3:24])[C:8](=[O:9])[N:10]([CH3:23])[C:11]=2[N:12]=[C:13]1[S:22][CH3:25])[CH3:21]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178468221HCID 178468221, compound

Product 1

HCID 54139417HCID 54139417, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring suspension of (R)-1-(5-hydroxyhexyl)-7-ethoxymethyl-8-mercapto-3-methylxanthine (62.0 mg, 0.174 mmol) and potassium carbonate (42 mg, 0.30 mmol) in acetonitrile (3.4 ml) was added methyl iodide (44 mg, 0.3 mmol). The reaction mixture was stirred at room temperature for 3 hours. After evaporation of the solvent under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (3:1) to provide (R)-7-ethoxymethyl-1-(5-hydroxyhexyl)-3-methyl-8-methylsulfanylxanthine (58 mg, 89% yield) as a white solid.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customThe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (3:1)

Sources & evidence

ORD record
ord-f1d57643b0a440239c5f4803cdac0deb
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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