Methyl iodide → HCID 24852340, compound

HRID 2235676Notes

Reaction equation

HRID 2235676 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12](/[CH:20]=[CH:21]/[C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]4)=[C:24]([O:34][CH3:35])[CH:23]=3)[N:13]3[CH2:18][CH2:17][NH:16][C:15](=[O:19])[C:14]=23)=[CH:6][CH:5]=1.CI.O.[C:39](=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12](/[CH:20]=[CH:21]/[C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]4)=[C:24]([O:34][CH3:35])[CH:23]=3)[N:13]3[CH2:18][CH2:17][N:16]([CH3:39])[C:15](=[O:19])[C:14]=23)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 24852339HCID 24852339, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 24852340HCID 24852340, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (containing mineral oil at 60%, 8 mg) was added to a solution of 1-(4-fluorophenyl)-3-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-6,7-dihydro-5H-imidazo[1,5-a]pyrazin-8-one (42 mg) in THF (3 mL), and the reaction solution was stirred at room temperature for 20 minutes. Methyl iodide (20 mg) was added to the reaction solution, and the reaction solution was stirred at room temperature for two hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: ethyl acetate->ethyl acetate:methanol=5:1) to obtain 10 mg of the title compound. The property values of the compound are as follows.

Workup

  1. stirringthe reaction solution was stirred at room temperature for two hours
  2. customthe organic layer was separated
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: ethyl acetate->ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-de8de7877e4240808cb4d4411d542303
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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