Potassium Carbonate → HCID 57477193, compound

HRID 1924008Notes

Reaction equation

HRID 1924008 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[C:8](=[O:11])([O-])[O-:9].[K+].[K+].Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)=O>CC(C)=O.C(OCC)(=O)C>[N:21]1[CH:22]=[CH:23][C:18]([C:16]2[N:1]=[C:2]3[CH2:7][N:6]([C:8]([O:9][C:18]([CH3:23])([CH3:19])[CH3:16])=[O:11])[CH2:5][CH2:4][N:3]3[CH:15]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 78747AminopyrazineHCID 4070312-Bromo-1-(pyridin-4-yl)ethanone

Product 1

HCID 57477193HCID 57477193, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-aminopyrazine (1.87 g) in dry acetone (30 ml) was added potassium carbonate (3 eqv), 4-bromoacetyl pyridine (2 eqv) and the resulting reaction mixture was heated at 60° C. for 20 hrs. Reaction mixture was filtered through a celite bed, residue washed with DCM and combined organic layer was evaporated completely to get a brown residue. It was again dissolved in ethyl acetate, washed with water and brine and finally dried over sodium sulfate. Evaporation of organic layer gave the crude product which was purified by column chromatography (1% methanol in dichloromethane). Yield: 12%, 30% Starting material recovered.

Workup

  1. customthe resulting reaction mixture
  2. customReaction mixture
  3. filtrationwas filtered through a celite bed, residue
  4. washwashed with DCM and combined organic layer
  5. customwas evaporated completely
  6. customto get a brown residue
  7. washwashed with water and brine
  8. dry with materialfinally dried over sodium sulfate
  9. customEvaporation of organic layer

Sources & evidence

ORD record
ord-0ca639a5d75341aca9cf868bb43b7645
Source dataset
uspto-grants-2012_05
Patent number
US08178535B2

Reaction notes

Loading…