Bromine → HCID 15546317, compound

HRID 2269089Notes

Reaction equation

HRID 2269089 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][CH3:13])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Br:21]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][CH3:13])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:21])[N:6]2[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 183326882-(Ethylthio)-9-(phenylmethyl)-9H-purin-6-amine

Product 1

HCID 15546317HCID 15546317, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-ethylthiopurine (214 mg, 0.75 mmol) and bromine (0.5 ml) were dissolved in 100 ml of methylene chloride and the solution was stirred at room temperature for 7 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 (43 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-9678f8667d5948c29dd6fb545802ab49
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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