Dimethyl Sulfoxide → HCID 14086958, compound

HRID 1502113Notes

Reaction equation

HRID 1502113 reaction equation
[CH3:1][S:2]([CH3:4])=O.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[Br:20][C:21]1[N:22]=[CH:23][C:24]([NH2:27])=[N:25][CH:26]=1>C(Cl)Cl>[Br:20][C:21]1[CH:26]=[N:25][C:24]([N:27]=[S:2]([CH3:4])[CH3:1])=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 5995392-Amino-5-bromopyrazine

Product 1

HCID 14086958HCID 14086958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a solution of DMSO (11 g, 138 mmol) in 100 mL of DCM was added Tf2O (42 g, 149 mmol) at −70° C. The resulting mixture was stirred at −70° C. for 15 minutes then a solution of 5-bromopyrazin-2-amine (20 g, 115 mmol, in 100 mL of DCM and 50 mL of DMSO) was added dropwise. The mixture was stirred at −60° C. for 3 hours and diluted with 500 mL of DCM and washed with water. The water layer was basified to pH=1 with aq. Na2CO3 and extracted with DCM twice. The combined DCM layer was washed with brine, dried over Na2SO4 and evaporated to afford title compound.

Workup

  1. stirringThe mixture was stirred at −60° C. for 3 hours
  2. washwashed with water
  3. extractionextracted with DCM twice
  4. washThe combined DCM layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-83d5e9d3a878409688c6954e2cdb2392
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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