Bromine → 2,6-Diamino-9-benzyl-8-bromopurine

HRID 2269123

Reaction equation

HRID 2269123 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([NH2:18])[N:3]=1.[Br:19]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([Br:19])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([NH2:18])[N:3]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 2389302,6-Diamino-9-benzylpurine

Product 1

HCID 183327282,6-Diamino-9-benzyl-8-bromopurineYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Diamino-9-benzylpurine (1.00 g, 4.16 mmol) and bromine (1 ml) were dissolved in 100 ml of methylene chloride and the solution was stirred at room temperature for 5 hours. Aqueous sodium thiosulfate was added to the reaction mixture. The organic layer was separated, dried on sodium 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 (0.62 g, yield 47%).

Workup

  1. customThe organic layer was separated
  2. customdried on sodium 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-3fac389c22814ac58bf04c7647325a06
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Linked notes

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