Potassium Carbonate → ethyl 1-(2-chloro-5-methylpyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carboxylate

HRID 539893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539893
[CH3:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[N:24]=[C:23](Cl)[C:22]([CH3:26])=[CH:21][N:20]=1>C(#N)C>[Cl:18][C:19]1[N:24]=[C:23]([N:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([CH3:1])=[N:3]2)[C:22]([CH3:26])=[CH:21][N:20]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 178469911HCID 178469911, Verbindung

Produkt 1

HCID 86698983ethyl 1-(2-chloro-5-methylpyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carboxylateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of ethyl 3-methyl-1H-pyrazole-4-carboxylate (4.7 g, 30.6 mmol) in acetonitrile were added potassium carbonate (10.6 g, 75.0 mmol) and 2,4-dichloro-5-methylpyrimidine (5.0 g, 30.6 mmol) at room temperature. The resulting suspension was heated at 80° C. for 3 hours with monitoring a reaction with LC-MS or thin layer chromatography (TLC). Volatiles were partially removed and the residue was extracted with ethyl acetate. The collected organic layer was washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting solid was recrystallized in a mixture of heptanes and ethyl acetate to afford the desired intermediate 5 as a pale yellow solid (5.2 g, 61%); MS (ESI) m/z 281 [M+H]+.

Aufarbeitung

  1. customa reaction with LC-MS or thin layer chromatography (TLC)
  2. customVolatiles were partially removed
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe collected organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was recrystallized in a mixture of heptanes and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a7e2341da63d4c7697e27c97ea4f45a8
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871778B2

Notizen zur Reaktion

Wird geladen…