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

HRID 3181

Reaction equation

HRID 3181 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-bfb87e53646f4c08bf6331ebf2a578a0
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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