Bromine → HCID 18332691, compound

HRID 2269129Notes

Reaction equation

HRID 2269129 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH:11][CH:12]([CH3:14])[CH3:13])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Br:22]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]([NH:11][CH:12]([CH3:14])[CH3:13])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:22])[N:6]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 18332720HCID 18332720, compound

Product 1

HCID 18332691HCID 18332691, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-(isopropylamino)purine (71 mg, 0.25 mmol) and bromine (0.5 ml) were dissolved in 50 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, 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 (73 mg, yield 81%).

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-b1ed30c5d5dd453db8922564ab65c81c
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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