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

HRID 2269158Notes

Reaction equation

HRID 2269158 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14]C)[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]([O:11][CH2:12][CH2:13][OH:14])[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 113355486-Amino-9-benzyl-2-(2-methoxyethoxy)purine

Product 1

HCID 183327916-Amino-9-benzyl-8-bromo-2-(2-hydroxyethoxy)purineYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-(2-methoxyethoxy)purine (100 mg, 0.36 mmol) and bromine (0.25 ml) were dissolved in methylene chloride (100 ml). The solution was stirred at room temperature for 6 hours. Aqueous sodium thiosulfate was added to the reaction mixture. The organic layer was separated, dried on sodium sulfate and the solvent was removed in vacuo. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (55 mg, yield 43%).

Workup

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

Sources & evidence

ORD record
ord-65d4561fbf9e4e24a3202b615b432822
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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