Bromine → HCID 11143619, compound

HRID 2269110Notes

Reaction equation

HRID 2269110 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Br:24]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][CH2:15][CH3:16])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:24])[N:6]2[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 18332792HCID 18332792, compound

Product 1

HCID 11143619HCID 11143619, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-pentoxypurine (95 mg, 0.305 mmol) and bromine (0.5 ml) were dissolved in 100 ml of methylene chloride and the solution was stirred at room temperature for 1 hour. Aqueous sodium thiosulfate was added to the reaction mixture. The organic layer was separated and dried on sodium sulfate and evaporated in vacuo to dryness. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (78 mg, yield 82%).

Workup

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

Sources & evidence

ORD record
ord-e64264699aca471380467480ba58573f
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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