2-(Benzenesulfonyl)-3-phenyloxaziridine → 5-Ethyl-4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamine

HRID 1356035Notes

Reaction equation

HRID 1356035 reaction equation
[CH2:1]([C:3]1[C:4]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[N:5][C:6]([NH2:11])=[N:7][C:8]=1[S:9][CH3:10])[CH3:2].C1(C2[O:25]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>ClCCl>[CH2:1]([C:3]1[C:4]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[N:5][C:6]([NH2:11])=[N:7][C:8]=1[S:9]([CH3:10])=[O:25])[CH3:2]

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 185072405-Ethyl-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine

Product 1

HCID 185073735-Ethyl-4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamineYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 350 mg (1.49 mmol) 5-ethyl-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine in 15 ml dichloromethane was added 780 mg (3.00 mmol) 3-phenyl-2-(phenylsulfonyl)oxaziridine and stirring continued for 16 hours at room temperature. The reaction mixture was then partitioned between dichloromethane and water and the phases separated. The organic phase was dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate then methanol/ethyl acetate 1/5) afforded 170 mg (46%) 5-ethyl-4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamine as a yellow crystalline solid. ES-MS m/e (%): 252 (M+H+, 100).

Workup

  1. customThe reaction mixture was then partitioned between dichloromethane and water
  2. customthe phases separated
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-242426acce804fd5beb437943701646a
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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