Water → HCID 67480197, compound

HRID 509542Notes

Reaction equation

HRID 509542 reaction equation
[Na].[CH3:2][CH:3]([S-:5])[CH3:4].Br[C:7]1[N:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1.O>CN(C=O)C>[CH:3]([S:5][C:7]1[N:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1)([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5995392-Amino-5-bromopyrazineHCID 86667788HCID 86667788, compound2×

Product 1

HCID 67480197HCID 67480197, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium-2-propanethiolate (2.256 g, 20.69 mmol) was added to a stirred solution of 5-bromopyrazin-2-amine (3 g, 17.24 mmol) in DMF (15 mL) and heated at 100° C. under microwave conditions for 4 hours. A further portion of sodium-2-propanethiolate (2.256 g, 20.69 mmol) was added the reaction heated for a further 1 hour at 100° C. under microwave conditions. Water was added and the mixture extracted with EtOAc (×2). The combined organic layers were washed with water (×3), brine (×1), dried, (MgSO4), filtered and concentrated in vacuo to give the sub-title compound as a beige oil which was used without further purification.

Workup

  1. temperatureheated for a further 1 hour at 100° C. under microwave conditions
  2. extractionthe mixture extracted with EtOAc (×2)
  3. washThe combined organic layers were washed with water (×3), brine (×1)
  4. dry with materialdried, (MgSO4),
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bcb8f9bdaa54147805dbe6044eaf208
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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