Potassium Carbonate → 1-(4-fluorophenyl)-3-methoxypyrazin-2(1H)-one

HRID 1676398Notes

Reaction equation

HRID 1676398 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[C:8]1[N:9]=[C:10]([O:22][CH3:23])[C:11](=[O:21])[N:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH:13]=1.[H][H]>CO.[Pd]>[F:20][C:17]1[CH:16]=[CH:15][C:14]([N:12]2[CH:13]=[CH:8][N:9]=[C:10]([O:22][CH3:23])[C:11]2=[O:21])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 673472395-chloro-1-(4-fluorophenyl)-3-methoxypyrazin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 224243451-(4-fluorophenyl)-3-methoxypyrazin-2(1H)-oneYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

K2CO3 (1.09 g, 7.85 mmol) and 10% Pd/C (0.42 g, 0.39 mmol) were added to 5-chloro-1-(4-fluorophenyl)-3-methoxypyrazin-2(1H)-one (2.0 g, 7.85 mmol) in MeOH (100 mL) at room temperature. Hydrogen gas was treated with balloon to the reaction mixture. After 6 hours stirring, the reaction mixture was filtered with MeOH and concentrated under reduced pressure. The crude was treated with CH2Cl2, washed with water, dried over MgSO4, and concentrated to give the desired product (1.55 g, 90%). LRMS (ESI pos) m/e 221.0 (M+1). 1H-NMR (400 MHz, CDCl3) δ 7.49 (m, 2H), 7.27 (t, 2H), 7.10 (d, 1H), 6.98 (d, 1H), 3.98 (s, 3H); 19F-NMR (376 MHz, CDCl3) δ −114.7.

Workup

  1. filtrationthe reaction mixture was filtered with MeOH
  2. concentrationconcentrated under reduced pressure
  3. additionThe crude was treated with CH2Cl2
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0833360c1e5d4563b91fa8038340d6b3
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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