Methyl iodide → HCID 19361732, compound

HRID 376290Notes

Reaction equation

HRID 376290 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:16]=[CH:15][NH:14][N:13]=2)[N:7]=1.[H-].[Na+].[CH3:19]I>CN(C)C=O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:16]=[CH:15][N:14]([CH3:19])[N:13]=2)[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178419958HCID 178419958, compound

Product 1

HCID 19361732HCID 19361732, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

2.50 g of 2-[1,3]dioxolan-2-yl-6-(1H-pyrazol-3-yl)pyridine (11.5 mmol) dissolved in 4 ml of N,N-dimethylformamide are added dropwise to a suspension of 0.48 g of sodium hydride (20 mmol) in 4 ml of N,N-dimethylformamide. The reaction mixture is stirred for 1 hour under a nitrogen atmosphere and then 0.93 ml of methyl iodide (15 mmol) diluted in 1 ml of N,N-dimethylformamide is added dropwise to the reaction mixture. The solution is stirred for 12 hours at room temperature and then the mixture is poured in ice-cold water and the mixture is extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: chloroform/methanol; 99:1). 0.83 g of a white solid is obtained.

Workup

  1. additionis added dropwise to the reaction mixture
  2. stirringThe solution is stirred for 12 hours at room temperature
  3. additionthe mixture is poured in ice-cold water
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e20d19c2cb8447df81cb0cb64278ca11
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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