Bromine → 6-Amino-9-benzyl-8-bromo-2-(3-ethoxypropoxy)purine

HRID 2269164Notes

Reaction equation

HRID 2269164 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH3:17])[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]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH3:17])[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 183327566-Amino-9-benzyl-2-(3-ethoxypropoxy)purine

Product 1

HCID 183327126-Amino-9-benzyl-8-bromo-2-(3-ethoxypropoxy)purineYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-(3-ethoxypropoxy)purine (354 mg, 1.08 mmol) and bromine (1.0 ml) were dissolved in methylene chloride (50 ml). 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 sodium sulfate and the solvent was removed. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (289 mg, yield 66%).

Workup

  1. customThe organic layer was separated
  2. customdried on sodium sulfate
  3. customthe solvent was removed
  4. customThe residue was purified with silica gel chromatography (1% methanol/chloroform)

Sources & evidence

ORD record
ord-75e18e2d7a184aaebf16efd709672249
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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