2-(Benzenesulfonyl)-3-phenyloxaziridine → 4-(Isopropylamino)-2-(methylsulfinyl)pyrimidine-5-carboxamide

HRID 2280777Notes

Reaction equation

HRID 2280777 reaction equation
[CH:1]([NH:4][C:5]1[C:10]([C:11]([NH2:13])=[O:12])=[CH:9][N:8]=[C:7]([S:14][CH3:15])[N:6]=1)([CH3:3])[CH3:2].C1(C2[O:24]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C(Cl)(Cl)Cl>[CH:1]([NH:4][C:5]1[C:10]([C:11]([NH2:13])=[O:12])=[CH:9][N:8]=[C:7]([S:14]([CH3:15])=[O:24])[N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridine2×HCID 709813214-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxamide

Product 1

HCID 709812914-(Isopropylamino)-2-(methylsulfinyl)pyrimidine-5-carboxamideYield 92.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirring solution of 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxamide (170 g, 0.751 mol) in chloroform (22 L) was added portion-wise 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (235.6 g, 0.902 mol) and the resulting solution was stirred at ambient temperature overnight. An additional amount of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (19.6 g, 0.075 mol) was added and the mixture was then stirred overnight at ambient temperature. The reaction solution was concentrated under reduced pressure to give the crude product as a white solid. The solids were triturated with ethyl acetate (1.5 L) at ambient temperature for 1 h, filtered, washed with ethyl acetate (250 mL), and dried in a vacuum oven overnight at 45° C. to afford 4-(isopropylamino)-2-(methylsulfinyl)pyrimidine-5-carboxamide (167.7 g, 92% yield) as white solid. MS (ESI) m/z 243.2 [M+1]+.

Workup

  1. stirringthe mixture was then stirred overnight at ambient temperature
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customto give the crude product as a white solid
  4. customThe solids were triturated with ethyl acetate (1.5 L) at ambient temperature for 1 h
  5. filtrationfiltered
  6. washwashed with ethyl acetate (250 mL)
  7. customdried in a vacuum oven overnight at 45° C.

Sources & evidence

ORD record
ord-b0f959d0033e447dad6775d73bb3ceef
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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