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

HRID 1360378Notes

Reaction equation

HRID 1360378 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(Cl)Cl.CO>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

6

Reactant 4

HCID 24408BromineHCID 706393-MethylxanthineHCID 517045Sodium AcetateHCID 21226129Dichloromethane methanol

Product 1

HCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

100 g of 3-methyl-3,7-dihydropurine-2,6-dione and 49 g of sodium acetate are suspended in 800 ml of glacial acetic acid and heated to an internal temperature of 90° C., and 33.3 ml of bromine are slowly (approx. 3-4 hours) added. The suspension is the stirred at this temperature for 3 hours when, according to TLC (DCM/MeOH 10:1), the reaction is complete. The reaction solution is cooled and filtered with suction. The residue is washed with 100 ml of glacial acetic acid and 500 ml of water and dried in vacuo at 50° C.

Workup

  1. custom(approx. 3-4 hours)
  2. additionadded
  3. temperatureThe reaction solution is cooled
  4. filtrationfiltered with suction
  5. washThe residue is washed with 100 ml of glacial acetic acid and 500 ml of water
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-7f94495a04c34d83a984d6bc2e0ca3b6
Source dataset
uspto-grants-2011_02
Patent number
US07879864B2

Reaction notes

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