Water → 8-isopropyl-4-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1893901Notes

Reaction equation

HRID 1893901 reaction equation
[CH:1]([N:4]1[C:9]2[N:10]=[C:11]([S:15][CH3:16])[N:12]=[C:13]([CH3:14])[C:8]=2[CH:7]=[CH:6][C:5]1=[O:17])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:26])C=1.[OH2:29]>C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>[CH:1]([N:4]1[C:9]2[N:10]=[C:11]([S:15]([CH3:16])(=[O:26])=[O:29])[N:12]=[C:13]([CH3:14])[C:8]=2[CH:7]=[CH:6][C:5]1=[O:17])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 576069628-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 576069728-isopropyl-4-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 11430Potassium CarbonateSolvent

Procedure

8-Isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (5.38 g, 21.59 mmol) was dissolved in 100 mL DCM. To the stirring solution, m-CPBA (13.97 g, 64.78 mmol) was added. The reaction was allowed to stir for 2.5 h at room temperature. LCMS indicated reaction had gone to completion. Sample was diluted with 300 mL of DCM and 300 mL K2CO3, upon addition of base a white precipitate formed that dissolved in excess H2O. Organic layer was extracted further with H2O and brine, and then dried over Na2CO3. The solvent was evaporated to afford the product 8-isopropyl-4-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one (6.0 g, 99% yield) as a light yellow oil that was used immediately in the next reaction.

Workup

  1. customreaction
  2. customformed
  3. extractionOrganic layer was extracted further with H2O and brine
  4. dry with materialdried over Na2CO3
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-83c21c40a7d34f449138f771508762cf
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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