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

HRID 1858225
Notes
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Reaction equation

HRID 1858225 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]([CH:21]([CH3:23])[CH3:22])[C:10]1=[O:24].ClC1C=CC=C(C(OO)=[O:33])C=1.[CH3:36][S:37]([CH3:39])=[O:38].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:36]([S:37]([CH3:39])(=[O:33])=[O:38])=[N:15][CH:16]=2)[N:11]([CH:21]([CH3:23])[CH3:22])[C:10]1=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 221250313-(2,6-dichlorophenyl)-1-isopropyl-7-methylthio-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 221249913-(2,6-dichlorophenyl)-1-isopropyl-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 60 mg (0.16 mmol) of 3-(2,6-dichlorophenyl)-1-isopropyl-7-methylthio-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one in 10 ml of dichloromethane was treated with 108 mg (0.32 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 and the phases were separated. The organic phase was washed with 30 ml of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to give 65 mg (100%) of 3-(2,6-dichlorophenyl)-1-isopropyl-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid. [Mass spectrum (ESI) MH+ =415].

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-dddb36db47fd462e8b451c3f08b4d200
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06150373

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes