Methyl iodide → HCID 59541030, compound

HRID 1677416Notes

Reaction equation

HRID 1677416 reaction equation
[CH:1]1([NH:6][C:7]2[CH:8]=[C:9]([C:13]3[N:14]=[C:15]4[C:21]([C:22]([C:24]5([CH3:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]5)=[O:23])=[CH:20][N:19]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:16]4=[N:17][CH:18]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:41]I>CN(C)C=O>[CH:1]1([N:6]([CH3:41])[C:7]2[CH:8]=[C:9]([C:13]3[N:14]=[C:15]4[C:21]([C:22]([C:24]5([CH3:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]5)=[O:23])=[CH:20][N:19]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:37])([CH3:36])[CH3:38])[C:16]4=[N:17][CH:18]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59541001HCID 59541001, compound

Product 1

HCID 59541030HCID 59541030, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [2-(3-Cyclopentylamino-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone in dimethyl formamide was added sodium hydride (60% dispersion in mineral oil, 9 mg, 0.218 mmol) under argon. The reaction mixture was stirred at room temperature for 15 minutes before the addition of methyl iodide via syringe. The reaction was stirred for 14 h before quenching with water and extracting 3 times with dichloromethane. The combined organics were washed with water, dried over MgSO4, filtered and concentrated in vacuo. Preparative thin layer chromatography (25% EtOAc/hexanes) afforded 0.0152 g (15% yield) of [2-[3-(Cyclopentyl-methyl-amino)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone as a yellow oil. MS (E/I): 547 (M+H)

Workup

  1. custombefore quenching with water
  2. extractionextracting 3 times with dichloromethane
  3. washThe combined organics were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d96ccfbabac4339b0cf54f3c280d132
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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