2-Amino-6-Chloropyrazine → 6-(Methylsulfanyl)pyrazin-2-amine

HRID 1857360Notes

Reaction equation

HRID 1857360 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[N:4][CH:3]=1.[CH3:9][S-:10].[Na+]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([S:10][CH3:9])[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 1184582-Amino-6-ChloropyrazineHCID 4378561Sodium methanethiolate

Product 1

HCID 221296536-(Methylsulfanyl)pyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A MIXTURE OF 6-AMINO-2-CHLOROPYRAZINE (5.2 G, 40 MMOL) AND SODIUM THIOMETHOXIDE (3.3 G, 47 MMOL) IN DRY DMF (30 ML) WERE HEATED IN A SEALED TUBE AT 100°C. FOR 16 H. THE REACTION WAS COOLED AND PARTITIONED BETWEEN WATER AND METHYLENE CHLORIDE. THE ORGANIC LAYER WAS DRIED (NA2SO4) AND EVAPORATED IN VACUO TO GIVE THE TITLE COMPOUND AS A CRYSTALLINE SOLID:

Workup

  1. temperatureTHE REACTION WAS COOLED
  2. customPARTITIONED BETWEEN WATER AND METHYLENE CHLORIDE
  3. customTHE ORGANIC LAYER WAS DRIED (NA2SO4)
  4. customEVAPORATED IN VACUO

Sources & evidence

ORD record
ord-84b0a9942d9b4cfaa126a20531b85933
Source dataset
uspto-grants-2000_11
Patent number
US06147078

Reaction notes

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