Methyl iodide → N-[5-[4-(benzyloxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-N,N',N'-trimethylurea

HRID 351251Notes

Reaction equation

HRID 351251 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:20]=[C:19]([NH:30][C:31]([N:33]([CH3:35])[CH3:34])=[O:32])[CH:18]=2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:36]I>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:20]=[C:19]([N:30]([CH3:36])[C:31]([N:33]([CH3:34])[CH3:35])=[O:32])[CH:18]=2)=[CH:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21091147N'-[5-[4-(benzyloxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-N,N-dimethylurea

Product 1

HCID 21091148N-[5-[4-(benzyloxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-N,N',N'-trimethylureaYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride 60% dispersion in mineral oil 93.1 mg was added in one portion to a solution of N-[5-[4-(benzyloxy)phenyl]-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-N′,N′-dimethylurea 1.43 g in DMF 10 ml under ice bath cooling. The reaction mixture was stirred at ambient temperature for 1 hour. MeI 688 mg was added the reaction mixture was stirred at ambient temperature overnight. The mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt-n-hexane=75%, 80% to give N-[5-[4-(benzyloxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-N,N′,N′-trimethylurea 1.45 g as an oil.

Workup

  1. temperaturecooling
  2. stirringwas stirred at ambient temperature overnight
  3. customThe mixture was partitioned between ethyl acetate and H2O
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluted with AcOEt-n-hexane=75%, 80%

Sources & evidence

ORD record
ord-846924037adf4a3e8d4ea07e7adbce07
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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