Potassium Carbonate → 8-Bromo-7-ethoxymethyl-3-methylxanthine

HRID 1355384Notes

Reaction equation

HRID 1355384 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(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][CH2:23]Cl)[CH3:21]>CN(C)C=O>[Br:1][C:2]1[N:10]([CH2:23][O:22][CH2:20][CH3:21])[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 11430Potassium CarbonateHCID 18523Chloromethyl ethyl etherHCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 224991168-Bromo-7-ethoxymethyl-3-methylxanthineYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of 8-bromo-3-methylxanthine (7.06 g, 28.8 mmol) and potassium carbonate (3.98 g, 28.8 mmol) in dimethylformamide (DMF) (150 ml) was added chloromethyl ethyl ether (2.72 g, 28.8 mmol). After stirring overnight at room temperature, the reaction mixture was poured into ice-cold water (650 ml). After stirring at 0-5° C. for 1 hour, the solid was filtered, washed with water (3×15 ml) and dried under vacuum to provide 8-bromo-7-ethoxymethyl-3-methylxanthine (6.15 g, 70% yield) as a white solid.

Workup

  1. stirringAfter stirring at 0-5° C. for 1 hour
  2. filtrationthe solid was filtered
  3. washwashed with water (3×15 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5232c3972e904cca87f580866c95ccf8
Source dataset
uspto-grants-2003_07
Patent number
US06586429B2

Reaction notes

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