Methyl iodide → 8-Bromo-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1835727Notes

Reaction equation

HRID 1835727 reaction equation
[Br:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[NH:7][C:6](=[O:12])[N:5]([CH3:13])[C:4]=2[N:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Br:1][C:2]1[N:10]([CH3:14])[C:9]2[C:8](=[O:11])[NH:7][C:6](=[O:12])[N:5]([CH3:13])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 7022428-Bromo-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dioneYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of 8-bromo-3-methylxanthine (prepared as described above for CT12440) (12.25 g, 50.0 mmol) and potassium carbonate (8.62 g, 62.5 mmol) in dimethylformamide (150 ml) was added methyl iodide (7.81 g, 55.0 mmol). After stirring overnight at room temperature, the mixture was poured into ice cold water (400 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 8-bromo-3,7-dimethylxanthine (12.10 g, 93% yield) as a beige 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-b10c9ede3c1345008b12f267197c0d9e
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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