2-(Benzenesulfonyl)-3-phenyloxaziridine → 4-(Bicyclo[1.1.1]pentan-1-ylamino)-2-(methylsulfinyl)pyrimidine-5-carboxamide

HRID 2280782Notes

Reaction equation

HRID 2280782 reaction equation
[C:1]12([NH:6][C:7]3[C:12]([C:13]([NH2:15])=[O:14])=[CH:11][N:10]=[C:9]([S:16][CH3:17])[N:8]=3)[CH2:5][CH:3]([CH2:4]1)[CH2:2]2.C1(C2[O:26]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:1]12([NH:6][C:7]3[C:12]([C:13]([NH2:15])=[O:14])=[CH:11][N:10]=[C:9]([S:16]([CH3:17])=[O:26])[N:8]=3)[CH2:2][CH:3]([CH2:5]1)[CH2:4]2

Participants

5

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 709820104-(Bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxamide

Product 1

HCID 709818504-(Bicyclo[1.1.1]pentan-1-ylamino)-2-(methylsulfinyl)pyrimidine-5-carboxamideYield 90.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxamide (76 g, 0.304 mol) in chloroform (7 L) was added 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (143 g, 0.547 mol, 1.8 equiv.) and the resulting pale yellow solution was stirred at ambient temperature overnight. The reaction solution was concentrated under reduced pressure to give the crude product as a white solid, which was diluted with ethyl acetate (1.5 L) and the slurry was stirred at room temperature for 1 h. The resulting suspension was filtered, washed with ethyl acetate, and dried under vacuum to afford the desired compound (73 g, 0.274 mol, 90% yield) as a white solid; MS (ESI): m/z 267.0 [M+1]+.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customto give the crude product as a white solid, which
  3. stirringthe slurry was stirred at room temperature for 1 h
  4. filtrationThe resulting suspension was filtered
  5. washwashed with ethyl acetate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-02820dceb42442d39ba774540caa5836
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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