Potassium Carbonate → HCID 15394823, compound

HRID 717116Notes

Reaction equation

HRID 717116 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[N:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[H][H]>C(O)C.[OH-].[Pd+2].[OH-]>[N:7]1[CH:2]=[CH:3][N:4]=[CH:5][C:6]=1[NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 61699828HCID 61699828, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15394823HCID 15394823, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolvent

Procedure

Ethyl 2-(6-chloropyrazin-2-ylamino)acetate (23.6 g, 109 mmol) was dissolved in non-denatured ethanol (250 mL) and potassium carbonate (15.13 g, 109 mmol) was added. The reaction was put under nitrogen and palladium hydroxide (3.84 g, 5.47 mmol) was added. The reaction was stirred under an atmosphere of hydrogen for 18 h. Additional palladium hydroxide (3.84 g, 5.47 mmol) was added and the reaction was charged with additional hydrogen and allowed to stir overnight. The reaction was filtered through Celite and the solvent was removed under reduced pressure to afford the title compound (15.13 g, 84 mmol, 76% yield). MS (ESI) m/z 182.3 [M+1]+.

Workup

  1. stirringto stir overnight
  2. filtrationThe reaction was filtered through Celite
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6b5a0a67c95a44e281b44a2408cb2f60
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

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