Methyl iodide → HCID 54327557, compound

HRID 1814986Notes

Reaction equation

HRID 1814986 reaction equation
[C:1]([O:4][C@H:5]([CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][C:16]([CH2:21][OH:22])=[N:15][C:14]=2[N:13]([CH3:23])[C:11]1=[O:12])(=[O:3])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[C:1]([O:4][C@H:5]([CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:25])[C:16]([CH2:21][OH:22])=[N:15][C:14]=2[N:13]([CH3:23])[C:11]1=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 54007388HCID 54007388, compound

Product 1

HCID 54327557HCID 54327557, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of (R)-1-(5-acetoxyhexyl)-8-hydroxymethyl-3-methylxanthine (6.35 g, 18.8 mmol) and potassium carbonate (5.2 g, 38 mmol) in dimethylformamide (55 ml) was added methyl iodide (4.0 g, 28.2 mmol). After stirring overnight at room temperature, the mixture was poured into ice cold water (250 ml) and stirred at 0-5° C. for 1 hour. The precipitate was filtered, rinsed with water (5×25 ml), and dried under vacuum to provide (R)-1-(5-acetoxyhexyl)-8-hydroxymethyl-3,7-dimethylxanthine (6.3 g, 95% yield) as a white solid.

Workup

  1. stirringstirred at 0-5° C. for 1 hour
  2. filtrationThe precipitate was filtered
  3. washrinsed with water (5×25 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6201c8fd929d4d31add737106f30bb83
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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