Dimethyl Sulfoxide → HCID 117769973, compound

HRID 1526381Notes

Reaction equation

HRID 1526381 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[C:4]=1[C:10]#[N:11].Br[CH2:13][CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O>[CH2:13]([N:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:10]#[N:11])[C:5]1=[O:9])[CH:14]([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65551-Bromo-2-methylpropaneHCID 10796Cesium carbonateHCID 27867023-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-2-oxo-

Product 1

HCID 117769973HCID 117769973, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (15.00 g), 1-bromo-2-methylpropane (21.4 g), cesium carbonate (65.2 g) and dimethyl sulfoxide (150 mL) was stirred at 50° C. for 24 hr. The reaction mixture was cooled to room temperature, and poured into water, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with ether to give the title compound (13.0 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe residue was washed with ether

Sources & evidence

ORD record
ord-9737f57e93cf4fd397abef165449fa10
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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