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

HRID 1858183Notes

Reaction equation

HRID 1858183 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 5 g (14.1 mmol) of 3-(2,6-dichlorophenyl)-7-methylthio-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one in 200 ml of dichloromethane was cooled in ice and treated with 10 g (28.9 mmol) of 3-chloroperbenzoic acid. 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. 100 ml of saturated aqueous sodium bicarbonate solution were 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-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one 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-e2b7883d17994db8854a9cb6fee99b04
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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