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Bromine → 6-Amino-9-benzyl-8-bromo-2-ethylaminopurine

HRID 2269125
Notes
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Reaction equation

HRID 2269125 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH:11][CH2:12][CH3:13])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Br:21]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]([NH:11][CH2:12][CH3:13])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:21])[N:6]2[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 183327806-Amino-9-benzyl-2-ethylaminopurine

Product 1

HCID 183327186-Amino-9-benzyl-8-bromo-2-ethylaminopurineYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Amino-9-benzyl-2-ethylaminopurine (75 mg, 0.28 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 (63 mg, yield 65%).

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-2b40ae7fa4d74bf58b8f85ad11a0b3bb
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