Bromine → HCID 15546319, compound

HRID 2269100Notes

Reaction equation

HRID 2269100 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([S:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Br:29]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:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:29])[N:6]2[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 18332726HCID 18332726, compound

Product 1

HCID 15546319HCID 15546319, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-(2-naphthylthio)purine (221 mg, 0.58 mmol) and bromine (0.4 ml) were dissolved in 160 ml of methylene chloride and the solution was stirred at room temperature for 5.5 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 (0.5% methanol/chloroform) to give the subject compound (118 mg, yield 44%).

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 (0.5% methanol/chloroform)

Sources & evidence

ORD record
ord-9fabec99245740719cda568a95154021
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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