Sulfuric acid magnesium salt (1:1) → [4-(2-Methanesulfonylpyrimidin-4-yl)-3-(3-methoxy-5-methylphenyl)-pyrazol-1-yl]acetonitrile

HRID 2390773Notes

Reaction equation

HRID 2390773 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[S:12]([O-:16])([O-])(=O)=[O:13].[Mg+2].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([C:27]2[C:31]([C:32]3[CH:37]=[CH:36][N:35]=[C:34](SC)[N:33]=3)=[CH:30][N:29]([CH2:40][C:41]#[N:42])[N:28]=2)[CH:23]=[C:24]([CH3:26])[CH:25]=1>ClCCl>[CH3:2][S:12]([C:34]1[N:33]=[C:32]([C:31]2[C:27]([C:22]3[CH:23]=[C:24]([CH3:26])[CH:25]=[C:20]([O:19][CH3:18])[CH:21]=3)=[N:28][N:29]([CH2:40][C:41]#[N:42])[CH:30]=2)[CH:37]=[CH:36][N:35]=1)(=[O:16])=[O:13]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 70297m-Chloroperbenzoic acidHCID 50899518[3-(3-Methoxy-5-methylphenyl)-4-(2-methylthio-pyrimidin-4-yl)pyrazol-1-yl]acetonitrile

Product 1

HCID 50899519[4-(2-Methanesulfonylpyrimidin-4-yl)-3-(3-methoxy-5-methylphenyl)-pyrazol-1-yl]acetonitrileYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (4.71 g, 27.3 mmol) and anhydrous magnesium sulfate (6.57 g, 54.6 mmol) in dichloromethane (100 mL) were dissolved at room temperature for 1 hour with stirring. To this solution was added [3-(3-methoxy-5-methylphenyl)-4-(2-methylthio-pyrimidin-4-yl)pyrazol-1-yl]acetonitrile (1.6 g, 4.55 mmol) which was subjected to oxidation to sulfone by stirring for an additional two hours. After completion of the reaction, the precipitate was filtered off and washed with dichloromethane. The filtrate was washed with brine and dichloromethane, and the organic layer was separated, dried over anhydrous magnesium sulfate and concentrated through vacuum distillation. The residue was purified by column chromatography to give the title compound (1.23 g, 70.4%).

Workup

  1. stirringby stirring for an additional two hours
  2. customAfter completion of the reaction
  3. filtrationthe precipitate was filtered off
  4. washwashed with dichloromethane
  5. washThe filtrate was washed with brine and dichloromethane
  6. customthe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated through vacuum distillation
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0fe15a6de46e426481ab01a836c9ac2b
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

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