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Bromine → 6-Amino-9-benzyl-8-bromo-2-(3-methylbutyl)thiopurine

HRID 2269096
Notes
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Reaction equation

HRID 2269096 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[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]([S:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 183327066-Amino-9-benzyl-2-(3-methylbutyl)thiopurine

Product 1

HCID 183327496-Amino-9-benzyl-8-bromo-2-(3-methylbutyl)thiopurineYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-(3-methylbutyl)thiopurine (260 mg, 0.79 mmol) and bromine (0.5 ml) were dissolved in 100 ml of methylene chloride and the solution was stirred at room temperature for 7 hours. Aqueous sodium thiosulfate was added to the reaction mixture. The organic layer was separated, dried on magnesium 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 (49 mg, yield 15%).

Workup

  1. customThe organic layer was separated
  2. customdried on magnesium 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-8116232453734045a80d1301edb302a3
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06329381B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes