Pyridine → 2-(4-Fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-propionic acid methyl ester

HRID 22662

Reaktionsgleichung

Reaktionsgleichung von HRID 22662
N1C=CC=CC=1.[CH3:7][O:8][C:9](=[O:28])[CH:10]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1)[OH:12]>C(Cl)Cl.CCOCC.[Cr]>[CH3:7][O:8][C:9](=[O:28])[CH:10]([C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1)=[O:12]

Komponenten

6

Edukt 2

HCID 1049PyridineHCID 129914022-(4-Fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-hydroxypropionic acid methyl ester

Produkt 1

HCID 129914032-(4-Fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-propionic acid methyl esterAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23976ChromiumKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of CrO3 in CH2Cl2 (300 mL) is added pyridine. The mixture is stirred vigorously for 1 hour at room temp. A solution of the crude 2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-hydroxypropionic acid methyl ester, 2, prepared above in CH2Cl2 (50 mL) is added dropwise to the chromium suspension. The reaction mixture is stirred at room temperature for 16 hours, diluted with ether (1 L) and filtered through a pad of Celite. The filtrate is concentrated in vacuo and the resulting residue is purified over silica (25% EtOAc/hexanes) to afford 3.7 g (43% yield) of the desired product as a yellow solid.

Aufarbeitung

  1. stirringThe reaction mixture is stirred at room temperature for 16 hours
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe resulting residue is purified over silica (25% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7097432dc3454a69a351135a03291a4a
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849627B2

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