Dimethyl Sulfoxide → (2-[3-[3-(2,6-dichlorophenyl)-7-methanesulfonyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester

HRID 1858318Notes

Reaction equation

HRID 1858318 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][C:8]([CH3:38])([CH3:37])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[C:21]3=[N:22]C(SC)=[N:24][CH:25]=[C:20]3[CH2:19][N:18]([C:28]3[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:35])[C:17]2=[O:36])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:48])C=1.[CH3:51][S:52]([CH3:54])=[O:53].C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:39])[NH:7][C:8]([CH3:38])([CH3:37])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[C:21]3=[N:22][C:51]([S:52]([CH3:54])(=[O:48])=[O:53])=[N:24][CH:25]=[C:20]3[CH2:19][N:18]([C:28]3[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:35])[C:17]2=[O:36])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 54285378(2-[3-[3-(2,6-dichlorophenyl)-7-methylthio-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 53757476(2-[3-[3-(2,6-dichlorophenyl)-7-methanesulfonyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 350 mg (0.6 mmol) of (2-[3-[3-(2,6-dichlorophenyl)-7-methylthio-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester in 10 ml of dichloromethane was treated with 400 mg (1.2 mmol) of 3-chloroperbenzoic acid (50% w/w water) and the mixture stirred for 3 hours. Dimethyl sulfoxide (0.5 ml) was added. After a further 10 minutes 10 ml of saturated aqueous sodium bicarbonate was added. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 370 mg (100%) of (2-[3-[3-(2,6-dichlorophenyl)-7-methanesulfonyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester as a white solid. [Mass spectrum (ESI) MH+ =620].

Workup

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

Sources & evidence

ORD record
ord-26dc4261ad9d45d0ac2b678ea8395beb
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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