Bromine → 8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1814924Notes

Reaction equation

HRID 1814924 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].C([O-])(=O)C.[Na+].[Br:18]Br>C(O)(=O)C>[Br:18][C:8]1[NH:7][C:6]2[C:5](=[O:11])[NH:4][C:3](=[O:12])[N:2]([CH3:1])[C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 706393-MethylxanthineHCID 517045Sodium Acetate

Product 1

HCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dioneYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a stirring suspension of 3-methylxanthine (7.9 g 47.6 mmol) and sodium acetate (7.81 g, 95.2 mmol) in glacial acetic acid (120 ml) was added bromine (9.14 g, 57.1 mmol). The mixture was stirred at 65° C. for 2 hours. After cooling to room temperature the precipitate was filtered, washed with acetic acid (2x 15 ml), water (3x 50 ml) and dried under vacuum to give 8-bromo-3-methylxanthine (10.5 g, 90% yield) as a beige powder.

Workup

  1. temperatureAfter cooling to room temperature the precipitate
  2. filtrationwas filtered
  3. washwashed with acetic acid (2x 15 ml), water (3x 50 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-db758aca39a74d64b2f17631f6cdbd77
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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