Bromine → HCID 15546318, compound

HRID 2269090Notes

Reaction equation

HRID 2269090 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][CH2:13][CH3:14])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Br:22]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][CH2:13][CH3:14])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:22])[N:6]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 12777823HCID 12777823, compound

Product 1

HCID 15546318HCID 15546318, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-propylthiopurine (290 mg, 0.97 mmol) and bromine (0.7 ml) were dissolved in 160 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 filtrate was evaporated in vacuo. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (58 mg, yield 16%).

Workup

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

Sources & evidence

ORD record
ord-f18c0f608f9d4e839b04ef636347d7e2
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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