Isopropylamine → 3-Chloro-N-(propan-2-yl)pyrazin-2-amine

HRID 333531Notes

Reaction equation

HRID 333531 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:9][CH:10]([NH2:12])[CH3:11]>C1COCC1>[Cl:8][C:7]1[C:2]([NH:12][CH:10]([CH3:11])[CH3:9])=[N:3][CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 785752,3-Dichloropyrazine

Product 1

HCID 214776373-Chloro-N-(propan-2-yl)pyrazin-2-amineYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3-dichloropyrazine (10 g, 67.1 mmol), propan-2-amine (11.90 g, 201 mmol), and 50 mL of THF were mixed in a three-neck flask and stirred at room temperature overnight. The reaction was brought to reflux overnight. The reaction was cooled and the solvent was evaporated. The residue was dissolved in dichloromethane and the salt was filtered. The solvent was then evaporated and the residue was purified by column using dichloromethane as solvent to give 3-chloro-N-isopropylpyrazin-2-amine (6.2 g, 53.8%).

Workup

  1. temperatureto reflux overnight
  2. temperatureThe reaction was cooled
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. filtrationthe salt was filtered
  6. customThe solvent was then evaporated
  7. customthe residue was purified by column

Sources & evidence

ORD record
ord-2f52f21493e84c5caa5d10d5da1134e0
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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