Bromine → HCID 18332721, compound

HRID 2269135Notes

Reaction equation

HRID 2269135 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])(=O)C.[Na+].[Br:30]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(O)(=O)C>[NH2:1][C:2]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:30])[N:6]2[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 517045Sodium AcetateHCID 18332798HCID 18332798, compound

Product 1

HCID 18332721HCID 18332721, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

6-Amino-2-anilino-9-benzylpurine (87 mg, 0.31 mmol) was dissolved in a mixture of methylene chloride (50 ml) and acetic acid (10 ml). To the solution were added sodium acetate (105 mg, 1.28 mmol) and bromine (0.5 ml), and the mixture was stirred at room temperature for 3 hour. Aqueous sodium thiosulfate was added to the reaction mixture. The organic layer was separated, washed with aqueous saturated sodium hydrogen carbonate, 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 (93 mg, yield 92%).

Workup

  1. customThe organic layer was separated
  2. washwashed with aqueous saturated sodium hydrogen carbonate
  3. customdried on sodium sulfate
  4. filtrationfiltered
  5. customThe solvent in the filtrate was evaporated in vacuo
  6. customThe residue was purified with silica gel chromatography (1% methanol/chloroform)

Sources & evidence

ORD record
ord-8583eff323924e089c7361f049924316
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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