Bromine → 6-Amino-9-benzyl-8-bromo-2-(3-hydroxypropoxy)purine

HRID 2269161Notes

Reaction equation

HRID 2269161 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][OH: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][CH2:14][OH: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 183327146-Amino-9-benzyl-2-(3-hydroxypropoxy)purine

Product 1

HCID 183327536-Amino-9-benzyl-8-bromo-2-(3-hydroxypropoxy)purineYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-(3-hydroxypropoxy)purine (210 mg, 0.7 mmol) and bromine (0.5 ml) were dissolved in methylene chloride (200 ml). The solution was stirred at room temperature for 4 hours. Aqueous sodium thiosulfate was added to the reaction mixture. The organic layer was separated, dried on magnesium sulfate and concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (5% methanol/chloroform) to give the subject compound (143 mg, yield 54%).

Workup

  1. customThe organic layer was separated
  2. customdried on magnesium sulfate
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue was purified with silica gel chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-eb0388bcdfce41e49f98aa62af845fcc
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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