Dimethyl Sulfoxide → 3-(2,6-dichlorophenyl)-7-methanesulfonyl-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1280554Notes

Reaction equation

HRID 1280554 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13]C(SC)=[N:15][CH:16]=2)[N:11]([CH3:21])[C:10]1=[O:22].ClC1C=CC=C(C(OO)=[O:31])C=1.[CH3:34][S:35]([CH3:37])=[O:36].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:34]([S:35]([CH3:37])(=[O:31])=[O:36])=[N:15][CH:16]=2)[N:11]([CH3:21])[C:10]1=[O:22]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 18425455HCID 18425455, compound

Product 1

HCID 184254443-(2,6-dichlorophenyl)-7-methanesulfonyl-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2,6-dichlorophenyl)-7-methylthio-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (1.1) (5 g, 14.1 mmol) in 200 mL of dichloromethane was cooled in ice and treated with 3-chloroperbenzoic acid (10 g, 28.9 mmol). The mixture was stirred at room temperature for 17 hours, then treated with 2 mL of dimethyl sulfoxide and left to stand for 10 minutes. Saturated aqueous sodium bicarbonate solution (100 mL) was then added and the phases were separated. The organic phase was dried over magnesium sulfate and filtered. Concentration of the filtrate under reduced pressure gave 5 g (92%) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (sulfone 1.2) as a white solid.

Workup

  1. waitleft
  2. waitto stand for 10 minutes
  3. customthe phases were separated
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bd8b89d25a6a4bc3b6d8354cb9f1e122
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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