Methyl iodide → HCID 21949811, compound

HRID 558286Notes

Reaction equation

HRID 558286 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[C:9]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])=[C:8]([CH2:19][CH3:20])[NH:7][N:6]=1)[CH3:4].[CH3:21]I>CN(C)C=O>[CH2:3]([C:5]1[C:9]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])=[C:8]([CH2:19][CH3:20])[N:7]([CH3:21])[N:6]=1)[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9813536HCID 9813536, compound

Product 1

HCID 21949811HCID 21949811, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil, 22 mg, 0.53 mmol) was added to a solution of the pyrazole from Example 60 (100 mg, 0.41 mmol) and methyl iodide (34 μl, 0.53 mmol) in dimethylformamide (1.5 ml) at 0° C. under nitrogen. The reaction was allowed to warm to room temperature and was stirred for 4 hours. The reaction was quenched with water and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (20 ml) and water (10 ml) and the organic phase was washed with water (2×10 ml), dried over magnesium sulphate and concentrated under reduced pressure. The residual oil was purified by flash chromatography on silica gel eluting with a solvent gradient of 100% pentane changing to 100% ethyl acetate and finally ethyl acetate:methanol (10:1, by volume) to provide the title compound (65 mg) as a colourless oil.

Workup

  1. customThe reaction was quenched with water
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (20 ml) and water (10 ml)
  4. washthe organic phase was washed with water (2×10 ml)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residual oil was purified by flash chromatography on silica gel eluting with a solvent gradient of 100% pentane changing to 100% ethyl acetate and finally ethyl acetate:methanol (10:1, by volume)

Sources & evidence

ORD record
ord-d0169f25e8e04003ac407ddfd06749a8
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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