1,2-Dimethoxyethane → 4-Chloro-5-ethyl-6-(furan-2-yl)-pyrimidine

HRID 1527640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527640
[Cl:1][C:2]1[C:7]([CH2:8][CH3:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1B(O)O.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:1][C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([C:12]2[O:11][CH:15]=[CH:14][CH:13]=2)[N:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 218284324,6-Dichloro-5-ethylpyrimidine

Produkt 1

HCID 656454164-Chloro-5-ethyl-6-(furan-2-yl)-pyrimidineAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4,6-dichloro-5-ethylpyrimidine (10 g), 2-furylboronic acid (6.33 g) tetrakis(triphenylphosphine)palladium (1.94 g), dimethoxyethane (100 ml), and sodium carbonate solution (2 mol/l) (60 ml) was stirred at 70° C. for 2 hours and at 80° C. for 2 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 6.06 g of 4-chloro-5-ethyl-6-(furan-2-yl)-pyrimidine.

Aufarbeitung

  1. temperatureto cool the reaction mixture to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-96d52de5ab5e426297f083d43a7a73b9
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09089136B2

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