Ethyl Acetate → 2-(Tert-butylamino)-4-(methylsulfinyl)pyrimidine-5-carboxamide

HRID 2280764Notes

Reaction equation

HRID 2280764 reaction equation
[C:1]([NH:5][C:6]1[N:11]=[C:10]([S:12][CH3:13])[C:9]([C:14]([NH2:16])=[O:15])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].C1(C2[O:25]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1.C(OCC)(=O)C>C(Cl)(Cl)Cl>[C:1]([NH:5][C:6]1[N:11]=[C:10]([S:12]([CH3:13])=[O:25])[C:9]([C:14]([NH2:16])=[O:15])=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 709813602-(Tert-butylamino)-4-(methylthio)pyrimidine-5-carboxamide

Product 1

HCID 709816072-(Tert-butylamino)-4-(methylsulfinyl)pyrimidine-5-carboxamideYield 86.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirring solution of 2-(tert-butylamino)-4-(methylthio)pyrimidine-5-carboxamide (0.1 g, 0.416 mmol) in chloroform (12 mL) was added portion-wise 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (0.130 g, 0.499 mmol). 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. Ethyl acetate (1 mL) was added and the slurry was stirred at room temp for 1 h. The solids were filtered, washed with ethyl acetate, and dried under vacuum to afford 2-(tert-butylamino)-4-(methylsulfinyl)pyrimidine-5-carboxamide (0.092 g, 0.359 mmol, 86% yield). MS (ESI) m/z 257.3 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-dd978b7acbe24de29ecec4e8bf2e5429
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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