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

HRID 882881Notes

Reaction equation

HRID 882881 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 added (about 3-4 hours). The suspension is then stirred at this temperature for 3 hours; the reaction is complete according to TLC (DCM/MeOH=10:1). 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 vacuum at 50° C.

Workup

  1. additionare slowly added (about 3-4 hours)
  2. temperatureThe reaction solution is cooled
  3. filtrationfiltered with suction
  4. washThe residue is washed with 100 ml of glacial acetic acid and 500 ml of water
  5. customdried in vacuum at 50° C.

Sources & evidence

ORD record
ord-47eaa561a3584bd0a9fc032d95c68c28
Source dataset
uspto-grants-2012_08
Patent number
US08236810B2

Reaction notes

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