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

HRID 1858199Notes

Reaction equation

HRID 1858199 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)[NH:11][C:10]1=[O:21].ClC1C=CC=C(C(OO)=[O:30])C=1.[CH3:33][S:34]([CH3:36])=[O:35].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:33]([S:34]([CH3:36])(=[O:30])=[O:35])=[N:15][CH:16]=2)[NH:11][C:10]1=[O:21]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 221250553-(2,6-dichlorophenyl)-7-methylthio-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 221250983-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 220 mg (0.64 mmol) of 3-(2,6-dichlorophenyl)-7-methylthio-3,4-dihydropyrimido[4,5-d]pyrimidine-2(1H)-one in 10 ml of dichloromethane was treated with 440 mg (1.28 mmol) of 3-chloroperbenzoic acid (50% w/w in water) and stirred for 18 hours. 0.2 ml of dimethyl sulfoxide was added. After a further 15 minutes 15 ml of saturated aqueous sodium bicarbonate solution were added. The phases were separated and then the organic phase was washed with 30 ml of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to give 250 mg (100%) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with 30 ml of saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-1cde9ece6bea41669b2a830071cc5d28
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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