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Methyl iodide → 2-Chloro-6-(3,4,5-trimethoxy-phenyl-amino)-9-methyl-9H-purine

HRID 9903
Notes
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Reaction equation

HRID 9903 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)[N:3]=1.[C:24](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:24])=[C:4]([NH:11][C:12]2[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 219881742-Chloro-6-(3,4,5-trimethoxy-phenyl-amino)-purine

Product 1

HCID 219882012-Chloro-6-(3,4,5-trimethoxy-phenyl-amino)-9-methyl-9H-purine

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

168 mg (0.5 mmol) of 2-chloro-6-(3,4,5-trimethoxy-phenyl-amino)-purine, 103 mg (0.75 mmol) of potassium carbonate and 0.156 ml (2.5 mmol) of methyl iodide are stirred in 3 ml of dimethylformamide at room temperature for 5 h. 30 ml of ethyl acetate are added to the slightly cloudy reaction solution and the mixture is extracted with water. The organic phase is dried over sodium sulfate. After removal of the solvent, the residue is recrystallized from ethyl acetate and diethyl ether. 2-Chloro-6-(3,4,5-trimethoxy-phenyl-amino)-9-methyl-9H-purine is obtained; FAB-MS: (M+H)+=350; Rf=0.6 (CH2Cl2:methanol=9:1).

Workup

  1. extractionthe mixture is extracted with water
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customAfter removal of the solvent
  4. customthe residue is recrystallized from ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-d4bf9e65b4ca4dc8a7893f11d1c680e7
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091346B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes