Methyl iodide → HCID 66758553, compound

HRID 1396807Notes

Reaction equation

HRID 1396807 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-69310ec2d01047059604ed3c1f83dad7
Source dataset
uspto-grants-2014_12
Patent number
US08901132B2

Reaction notes

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