Bromine → HCID 11099680, compound

HRID 2269107Notes

Reaction equation

HRID 2269107 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Br:20]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:20])[N:6]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 13810038HCID 13810038, compound

Product 1

HCID 11099680HCID 11099680, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-methoxypurine (118 mg, 0.46 mmol) and bromine (0.5 ml) were dissolved in 50 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 evaporated in vacuo to dryness. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (90 mg, yield 58%).

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-a3e996afff914ec7a76067d2913ada22
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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