2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 68858127, compound

HRID 1783534Notes

Reaction equation

HRID 1783534 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]=1

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 688614513-(3,5-Dimethoxyphenyl)-1-ethyl-7-(methylsulfanyl)-3,4-dihydropyrimido[4,5-D]pyrimidin-2(1H)-one

Product 1

HCID 68858127HCID 68858127, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

Workup

  1. washwashed with brine and water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluting with a solvent mixture of 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-1fc1d0f6e1a44b70bf9dc9cc9623396a
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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