Bromine → HCID 18332771, compound

HRID 2269098Notes

Reaction equation

HRID 2269098 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Br:25]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:25])[N:6]2[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 18332754HCID 18332754, compound

Product 1

HCID 18332771HCID 18332771, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-phenylthiopurine (95 mg, 0.28 mmol) and bromine (0.4 ml) were dissolved in 150 ml of methylene chloride and the solution was stirred at room temperature for 4.5 hours. Aqueous sodium thiosulfate was added to the reaction mixture. The organic layer was separated, dried on magnesium sulfate and filtered. The solvent in the filtered was evaporated in vacuo. The residue was purified with silica gel chromatography (0.5% methanol/chloroform) to give the subject compound (25 mg, yield 22%).

Workup

  1. customThe organic layer was separated
  2. customdried on magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent in the filtered was evaporated in vacuo
  5. customThe residue was purified with silica gel chromatography (0.5% methanol/chloroform)

Sources & evidence

ORD record
ord-694d35035c5b4dc6b3aec9c670aa592e
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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