Potassium Carbonate → HCID 50899431, compound

HRID 2390769Notes

Reaction equation

HRID 2390769 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([O:20][CH3:21])[CH:14]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[C:4]([NH:22][CH2:23][C@@H:24]([OH:26])[CH3:25])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:34][C:35]#[N:36]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([O:20][CH3:21])[CH:14]=3)=[N:10][N:11]([CH2:34][C:35]#[N:36])[CH:12]=2)[CH:5]=[C:4]([NH:22][CH2:23][C@@H:24]([OH:26])[CH3:25])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69356IodoacetonitrileHCID 178490034HCID 178490034, compound

Product 1

HCID 50899431HCID 50899431, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a two-necked round-bottom flask, 4-[2-chloro-6-(2(S)-hydroxypropylamino)-pyrimidin-4-yl]-3-(3-methoxy-5-methylphenyl)-1H-pyrazol (900 mg, 2.4 mmol) was dissolved in acetone (30 mL) to which finely ground potassium carbonate (1.66 g, 12 mmol) was then added and refluxed for 2 hours. Iodoacetonitrile (0.2 mL, 3.36 mmol) was dropwise added, followed by reflux for an additional 2 hours. After completion of the reaction, the solvent was removed by vacuum distillation. The reaction mixture was dissolved in water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed by vacuum distillation and the residue was purified through column chromatography to produce the title compound (430 mg, 43.4%).

Workup

  1. additionwas then added
  2. temperaturerefluxed for 2 hours
  3. temperatureby reflux for an additional 2 hours
  4. customAfter completion of the reaction
  5. customthe solvent was removed by vacuum distillation
  6. dissolutionThe reaction mixture was dissolved in water
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was removed by vacuum distillation
  11. customthe residue was purified through column chromatography

Sources & evidence

ORD record
ord-d0895aabd88c48caa8b5f64ce511d914
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

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