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

HRID 2269169Notes

Reaction equation

HRID 2269169 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[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][O:14][CH3:15])[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 183327586-Amino-9-benzyl-8-bromo-2-(2-methoxyethoxy)purineYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-(2-methoxyethoxy)purine (93 mg, 0.31 mmol) and bromine (1 ml) were dissolved in methylene chloride (100 ml). The solution was stirred at room temperature for 1 hour. Aqueous sodium thiosulfate was added to the reaction mixture. The organic layer was separated, dried on sodium sulfate and concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (75 mg, yield 64%).

Workup

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

Sources & evidence

ORD record
ord-e1f8d962dea24689b7bc2cdf8878da21
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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