Dimethyl Sulfoxide → 6-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1586419Notes

Reaction equation

HRID 1586419 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[C:20]1[C:31](=[O:32])[N:30]([CH3:33])[C:23]2[N:24]=C(SC)[N:26]=[CH:27][C:22]=2[CH:21]=1.[CH3:34][S:35]([CH3:37])=[O:36]>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[C:20]1[C:31](=[O:32])[N:30]([CH3:33])[C:23]2[N:24]=[C:34]([S:35]([CH3:37])(=[O:9])=[O:36])[N:26]=[CH:27][C:22]=2[CH:21]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 107367016-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A quantity of 0.346 g (1.00 mmol) of 50% to 60% m-chloroperbenzoic acid (assuming 50% peracid was present) was added at 25° C. to a stirred solution of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 in 15 mL of chloroform, and the solution was stirred overnight. A quantity of 0.25 g (3.20 mmol) of dimethylsulfoxide was added to reduce any excess peracid. After 15 minutes, the chloroform solution was washed with 30 mL of saturated sodium bicarbonate and then with water. The separated organic layer was dried over sodium sulfate, filtered, and concentrated to ca. 5 mL volume. Crystals separated. Added ca. 5 mL of petroleum ether and filtered; wt 0.165 g (92%); mp>290° C.

Workup

  1. waitAfter 15 minutes
  2. washthe chloroform solution was washed with 30 mL of saturated sodium bicarbonate
  3. dry with materialThe separated organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to ca. 5 mL volume
  6. customCrystals separated
  7. additionAdded ca. 5 mL of petroleum ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-d08bd59c2f7d4efcbf706d4ed54927a3
Source dataset
uspto-grants-1999_08
Patent number
US05945422

Reaction notes

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