2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 68858127, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[CH2:20][C:19]3[C:14](=[N:15][C:16]([S:21][CH3:22])=[N:17][CH:18]=3)[N:13]([CH2:23][CH3:24])[C:12]2=[O:25])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C1(C2[O:34]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[CH2:20][C:19]3[C:14](=[N:15][C:16]([S:21]([CH3:22])=[O:34])=[N:17][CH:18]=3)[N:13]([CH2:23][CH3:24])[C:12]2=[O:25])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1Participants
4
Procedure
To a solution of 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfanyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one (5.61 g, 15.57 mmol) in dichloromethane (100 mL) at ambient temperature was added 3-phenyl-2-(phenylsulfonyl)oxaziridine (4.88 g, 18.69 mmol, PD 0191006, Org. Synth., 1987; 66:203-210) in portions. The reaction mixture was stirred overnight, then washed with brine and water. The organic layer was dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by column chromatography eluting with a solvent mixture of 3% methanol in dichloromethane to yield 4.6 g (78%) of the titled compound: mp 167-169° C. Mass Spectrum (APCI, 80/20 CH3CN/H2O, Probe=450° C.) (m+1)/z 377.1