Diethyl Ether → 1-(5-(2-Chloro-4-morpholino-quinazolin-7-yl)furan-2-yl)ethanol

HRID 517472

Reaktionsgleichung

[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([C:18]3[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1.[CH3:25][Mg]Br.C(OCC)C>C1COCC1>[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[C:9]2[C:4](=[CH:5][C:6]([C:18]3[O:22][C:21]([CH:23]([OH:24])[CH3:25])=[CH:20][CH:19]=3)=[CH:7][CH:8]=2)[N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a 50 mL round bottom flask, 5-(2-chloro-4-morpholino-quinazolin-7-yl)furan-2-carbaldehyde (0.5 g, 0.001457 mol) and THF (25 mL) was added and cooled to 0° C. To the flask was slowly added 1.5 M methyl magnesium bromide in diethyl ether (0.145 mL, 0.002186 mol). The resulting reaction mixture was stirred at room temperature for 3 h. The reaction was quenched with water and extracted with ethyl acetate (3×50 mL). The organic layer was dried over anhydrous sodium sulfate and evaporated to provide the crude product. The crude product was purified by column chromatography using 60-120 silica gel and 40% ethyl acetate in hexane [0.3 g, 57%]. 1H NMR (300 MHz, CDCl3): δ 8.05 (d, J=1.2 Hz, 1H), 7.83 (d, J=6.3 Hz, 1H), 7.71 (dd, J′=6.6, J″=1.2 Hz, 1H), 6.82 (d, J=2.4 Hz, 1H), 6.40 (d, J=2.7 Hz, 1H), 4.91 (q, J=4.8 Hz, 1H), 3.89 (s, 8H), 1.63 (d, J=4.8 Hz, 3H). LC-MS (ESI): Calculated mass: 359.1; Observed mass: 360.1 (RT: 1.58 min).

Aufarbeitung

customThe resulting reaction mixture
customThe reaction was quenched with water
extractionextracted with ethyl acetate (3×50 mL)
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-1f650f50d1bd45f3b442790985335761
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09115092B2

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