Bromine → HCID 18332768, compound

HRID 2269094Notes

Reaction equation

HRID 2269094 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH:12]([CH2:14][CH3:15])[CH3:13])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Br:23]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH:12]([CH2:14][CH3:15])[CH3:13])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:23])[N:6]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 18332711HCID 18332711, compound

Product 1

HCID 18332768HCID 18332768, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-(sec-butylthio)purine (60 mg, 0.19 inmol) and bromine (0.4 ml) were dissolved in 85 ml of methylene chloride and the solution was stirred at room temperature for 2 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 (chloroform) to give the subject compound (53 mg, yield 71%).

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 (chloroform)

Sources & evidence

ORD record
ord-bd99c0a3961a4b26b8f375b8b3bd5d5b
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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