Methyl iodide → HCID 54318714, compound

HRID 1814937Notes

Reaction equation

HRID 1814937 reaction equation
[H-].[Na+].[C:3]([O:6][C@H:7]([CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[NH:19][N:18]=[N:17][C:16]=2[N:15]([CH3:23])[C:13]1=[O:14])(=[O:5])[CH3:4].[CH3:25]I>CS(C)=O>[C:3]([O:6][C@H:7]([CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:25])[N:18]=[N:17][C:16]=2[N:15]([CH3:23])[C:13]1=[O:14])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178476621HCID 178476621, compound

Product 1

HCID 54318714HCID 54318714, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of sodium hydride (22 mg, 0.91 mmol) in anhydrous dimethylsulfoxide (4.0 ml) was added (R)-1-(5-acetoxyhexyl)-3-methyl-8-azaxanthine (225 mg, 0.728 mmol). After stirring at room temperature for 30 min, the mixture was treated with methyl iodide (524 mg, 3.64 mmol). After stirring at room temperature overnight, the reaction was quenched by addition of saturated aqueous sodium chloride solution (20 ml) and then extracted with ethyl acetate (3x 15 ml). The combined extracts were washed with water (10 ml), with saturated aqueous sodium chloride solution (10 ml) and dried over magnesium sulfate. TLC showed that there were two products in this mixture. After evaporation of the solvent under reduced pressure, the crude products were purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1) to provide (R)-1-(5-acetoxyhexyl)-3,7-dimethyl-8-azaxanthine (74 mg, 31% yield) followed by (R)-1-(5-acetoxyhexyl)-3,8-dimethyl-8-azaxanthine (66 mg, 28% yield).

Workup

  1. stirringAfter stirring at room temperature overnight
  2. customthe reaction was quenched by addition of saturated aqueous sodium chloride solution (20 ml)
  3. extractionextracted with ethyl acetate (3x 15 ml)
  4. washThe combined extracts were washed with water (10 ml), with saturated aqueous sodium chloride solution (10 ml)
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent under reduced pressure
  7. customthe crude products were purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-1c293e61f0aa4bbeb75335c8419bd670
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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