Sodium Carbonate → Methyl 3-methoxy-6-methylpyrazine-2-carboxylate

HRID 890048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890048
Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][CH3:13])=[N:4][CH:3]=1.[CH3:14][Zn]C.[Cl-].[NH4+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:13][O:12][C:5]1[C:6]([C:8]([O:10][CH3:11])=[O:9])=[N:7][C:2]([CH3:14])=[CH:3][N:4]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 22248028Methyl 6-bromo-3-methoxypyrazine-2-carboxylateHCID 178477796HCID 178477796, Verbindung

Produkt 1

HCID 22247866Methyl 3-methoxy-6-methylpyrazine-2-carboxylateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418745HCID 178418745, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After dissolving 300 mg of methyl 6-bromo-3-methoxypyrazine-2-carboxylate in 10 ml of tetrahydrofuran, 32 mg of [1,3-bis(diphenylphosphino)propane]dichloronickel(II) was added, a solution of 0.73 ml of dimethyl zinc in toluene (2.0 M) was added dropwise under a nitrogen atmosphere and the mixture was stirred at room temperature for 3 hours. Saturated aqueous ammonium chloride solution and aqueous sodium carbonate solution were added to the reaction solution in that order, and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (161 mg, 73% yield).

Aufarbeitung

  1. additionwas added
  2. washThe organic layer was washed with water and saturated brine in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fd19ce22ec464e0b8af224bdf6012d46
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995144B2

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