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

HRID 2241371Notes

Reaction equation

HRID 2241371 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>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

5

Reactant 2

HCID 11430Potassium CarbonateHCID 673472395-chloro-1-(4-fluorophenyl)-3-methoxypyrazin-2(1H)-one

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 under a H2 atmosphere and the reaction was stirred for 6 hours. 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).

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-d3fb530f86a9449aab13af856901e781
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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