Water → 3-Bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

HRID 68653Notes

Reaction equation

HRID 68653 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:20][C:15]1[C:16]([NH2:19])=[N:17][CH:18]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:5])=[O:6])=[CH:8][CH:9]=2)[N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 580843825-(4-(Isopropylsulfonyl)phenyl)pyrazin-2-amine

Product 1

HCID 580843723-Bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amineYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(4-(Isopropylsulfonyl)phenyl)pyrazin-2-amine (10 g, 36.06 mmol) was dissolved in dry DMF (70 mL) and N-bromosuccinimide (6.418 g, 36.06 mmol) was added portionwise. The mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured into water (200 mL) and stirred for 5 minutes. The solid was isolated by filtration and washed with water. The wet solid was dissolved in ethyl acetate and any insoluble material removed by filtration. The aqueous layer was separated and the organic phase washed with saturated aqueous Na2S2O3 (×1) and dried (MgSO4). The organic extracts were filtered through a plug of Florisil (200 mesh), eluting with ethyl acetate. The filtrate was concentrated to ca. 50 mL and resultant precipitate isolated by filtration and washed with Petroleum Ether. The solid was further dried under high vacuum to give the sub-title compound as a pale orange solid (8.0 g, 62% Yield).). 1H NMR (400.0 MHz, DMSO) δ 1.17 (d, 6H), 3.41-3.49 (m, 1H), 7.16 (br s, 2H), 7.89 (d, 2H), 8.17 (d, 2H) and 8.76 (s, 1H) ppm; MS (ES+) 356.1.

Workup

  1. stirringstirred for 5 minutes
  2. customThe solid was isolated by filtration
  3. washwashed with water
  4. dissolutionThe wet solid was dissolved in ethyl acetate
  5. customany insoluble material removed by filtration
  6. customThe aqueous layer was separated
  7. washthe organic phase washed with saturated aqueous Na2S2O3 (×1)
  8. dry with materialdried (MgSO4)
  9. filtrationThe organic extracts were filtered through a plug of Florisil (200 mesh)
  10. washeluting with ethyl acetate
  11. concentrationThe filtrate was concentrated to ca. 50 mL and resultant
  12. customprecipitate
  13. customisolated by filtration
  14. washwashed with Petroleum Ether
  15. customThe solid was further dried under high vacuum

Sources & evidence

ORD record
ord-4e222c9f31694e54a48e09b89eb5a4a2
Source dataset
uspto-grants-2014_09
Patent number
US08822469B2

Reaction notes

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