Dimethyl Sulfoxide → HCID 22125044, compound

HRID 1858332Notes

Reaction equation

HRID 1858332 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13]C(SC)=[N:15][CH:16]=2)[N:11]([C:21]2[CH:22]=[C:23]([CH2:27][CH2:28][CH2:29][N:30]3[C:38](=[O:39])[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:31]3=[O:40])[CH:24]=[CH:25][CH:26]=2)[C:10]1=[O:41].ClC1C=CC=C(C(OO)=[O:50])C=1.[CH3:53][S:54]([CH3:56])=[O:55].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:53]([S:54]([CH3:56])(=[O:50])=[O:55])=[N:15][CH:16]=2)[N:11]([C:21]2[CH:22]=[C:23]([CH2:27][CH2:28][CH2:29][N:30]3[C:38](=[O:39])[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:31]3=[O:40])[CH:24]=[CH:25][CH:26]=2)[C:10]1=[O:41]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22125173HCID 22125173, compound

Product 1

HCID 22125044HCID 22125044, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 180 mg (0.3 mmol) of 2-[3-[3-[3-(2,4-dichlorophenyl)-7-methylthio-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-propyl]-isoindole-1,3-dione in 10 ml of dichloromethane was treated with 200 mg (0.6 mmol) of 3-chloroperbenzoic acid (50% w/w water) and the mixture stirred at ambient temperature for 18 hours. 0.1 ml of dimethyl sulfoxide was added. After a further 15 minutes 10 ml of dichloromethane and 20 ml of saturated aqueous sodium bicarbonate were added. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 190 mg (100%) of 2-[3-[3-[3-(2,4-dichlorophenyl)-7-methanesulfonyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-propyl]-isoindole-1,3-dione as a white solid. [Mass spectrum (ESI) MH+ =636].

Workup

  1. dry with materialThe organic phase was dried over magnesium sulfate
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-3ec9fd6d50b44440b450f6c93040a13d
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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