Sodium Hydroxide → HCID 14052172, compound

HRID 1030789Notes

Reaction equation

HRID 1030789 reaction equation
[SH:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][CH:10]=[CH:11][C:5]2=[N:4][C:3]=1[CH3:12].Cl.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20]Cl.[OH-].[Na+]>C(O)C>[CH3:12][C:3]1[N:4]=[C:5]2[CH:11]=[CH:10][CH:9]=[N:8][C:6]2=[N:7][C:2]=1[S:1][CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 178432200HCID 178432200, compound

Product 1

HCID 14052172HCID 14052172, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.67 g of 3-mercapto-2-methylpyrido[2,3-b]pyrazine were added 10 ml of ethanol and a solution of 1.15 g of 2-picolyl chloride hydrochloride and 0.67 g of sodium hydroxide. The obtained mixture was heated under refluxing for 1.5 hrs, and then the solvent was removed under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with water and saturated aqueous sodium chloride solution, and dried over sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was placed under reduced pressure to remove the solvent. The residue was dissolved in 20 ml of acetonitrile, and the insolubles were removed by filtration. The filtrate was concentrated to give 1.5 g of 2-methyl-3-(2-pyridylmethylthio)pyrido[2,3-b]pyrazine as a brown oil.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder refluxing for 1.5 hrs
  3. customthe solvent was removed under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washThe extract was washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customThe sodium sulfate was removed by filtration
  8. customto remove the solvent
  9. dissolutionThe residue was dissolved in 20 ml of acetonitrile
  10. customthe insolubles were removed by filtration
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0c5724253e874e2aa84d9f00d66107e2
Source dataset
uspto-grants-1992_04
Patent number
US05106976

Reaction notes

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