Acetyl chloride → HCID 59694012, compound

HRID 2199311Notes

Reaction equation

HRID 2199311 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:9](Cl)(=[O:11])[CH3:10]>C1COCC1>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 3132155-Methylpyrazin-2-amine

Product 1

HCID 59694012HCID 59694012, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methylpyrazin-2-amine (300 mg, 2.75 mmol) in dried THF (9 mL) were added acetyl chloride (0.21 mL, 2.89 mmol) and TEA (0.75 mL, 5.50 mmol). The reaction mixture was stirred for 3 hours after which, it was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (10% to 30% Ethyl acetate/Hexane) as a solvent to afford title compound (360 mg, 86% yield). MS m/z: 152 [M+1].

Workup

  1. customwas partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4, celite
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-ed63630d56704e8a8dca252a9027f399
Source dataset
uspto-grants-2016_06
Patent number
US09358231B2

Reaction notes

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