Methyl iodide → HCID 66758553, compound

HRID 718330Notes

Reaction equation

HRID 718330 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[NH:8]2)=[C:4]([N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:34])[CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[CH2:20][CH2:19]2)[N:3]=1.[C:35](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:8]2[CH3:35])=[C:4]([N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:34])[CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[CH2:20][CH2:19]2)[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178508586HCID 178508586, compound

Product 1

HCID 66758553HCID 66758553, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-6-[4-(4-chlorophenoxyacetyl)piperazin-1-yl]-8-(4-fluorophenyl)-9H-purine (48 mg, 0.1 mmol) in DMF (2 ml) was added potassium carbonate (28 mg, 0.2 mmol) and methyl iodide (6 μl, 0.1 mmol). The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was evaporated in vacuo and the crude residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1:50), yielding the pure title compound (40 mg, 80%).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe crude residue was purified by flash chromatography on silica
  3. additiona mixture of methanol and dichloromethane (in a ratio of 1:50),

Sources & evidence

ORD record
ord-635972331f7349c9ad9730650766d474
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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