Tetrahydrofuran → 2-[5-(4-Isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrimidine-5-carbaldehyde
Reaktionsgleichung
C([Li])CCC.Cl[C:7]1[CH:8]=[N:9][C:10]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[N:11][CH:12]=1.C1C[O:31][CH2:30]C1>CN(C=O)C>[CH2:24]([C:21]1[CH:22]=[CH:23][C:18]([C:16]2[O:15][N:14]=[C:13]([C:10]3[N:9]=[CH:8][C:7]([CH:30]=[O:31])=[CH:12][N:11]=3)[N:17]=2)=[CH:19][CH:20]=1)[CH:25]([CH3:27])[CH3:26]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
n-Butyllithium (4.77 mL, 7.16 mmol) was added to a solution of 5-chloro-2-[5-(4-isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrimidine (1.5 g, 4.77 mmol) and THF (50 mL) at −78° C. and stirred for 7 hours DMF (3 mL) was added to the reaction mixture, warmed to 0° C. and stirred for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL) and stirred at room temperature for 12 hours. The reaction mixture was diluted with EtOAc (25 mL) and the organic layer was separated and washed with water (3×25 mL) and brine (1×25 mL) and concentrated in vacuo to provide the title compound (1.13 g, 76% yield) as an orange solid.
Aufarbeitung
- additionwas added to the reaction mixture
- customThe reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL)
- stirringstirred at room temperature for 12 hours
- additionThe reaction mixture was diluted with EtOAc (25 mL)
- customthe organic layer was separated
- washwashed with water (3×25 mL) and brine (1×25 mL)
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-de8ab14b3d924962abfc769dbb8f72f4
- Quelldatensatz
- uspto-grants-2010_03
- Patentnummer
- US07671043B2
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