Reaktion #604648

Reaktionsgleichung

7-bromo-2-chloro-4-morpholin-4-yl-quinazoline

5-formyl-2-furanylboronic acid

sodium carbonate

toluene

→

desired product

Ausbeute 69.0%

5-(2-chloro-4-morpholino-quinazolin-7-yl)furan-2-carbaldehyde

Ausbeute 69.0%

Lösungsmittel

water

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was degassed with nitrogen for 5-10 min
2. 2
   Sonstigeagain degassed with nitrogen for 5-10 min
3. 3
   TemperaturThe reaction mixture was cooled
4. 4
   workup.ADDITIONdiluted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with water, brine
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   SonstigeThe solvent was removed under reduced pressure
8. 8
   Sonstigeto afford the crude product
9. 9
   SonstigeThe crude product was purified

Vorschrift

To a 50 mL round bottom flask, 7-bromo-2-chloro-4-morpholin-4-yl-quinazoline (Example 1; 1.0 g, 0.00304 mol) and 5-formyl-2-furanylboronic acid (0.384 g, 0.00274 mol), sodium carbonate (0.806 g, 0.0076 mol), toluene (15 mL), EtOH (15 mL) and water (5 mL) were added. The reaction mixture was degassed with nitrogen for 5-10 min. To the same reaction mixture, Pd(PPh3)2Cl2 (0.105 g, 0.000152 mol) was added and again degassed with nitrogen for 5-10 min. The reaction mixture was stirred at 75° C. for 2.5 h. The reaction mixture was cooled and diluted with ethyl acetate. The organic layer was washed with water, brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford the crude product. The crude product was purified; using column chromatography (60-120 silica gel, 75% ethyl acetate in hexane) to yield the desired product [0.65 g, 62%]. 1H NMR (300 MHz, CDCl3): δ 9.73 (s, 1H), 8.20 (s, 1H), 7.90 (s, 2H), 7.38 (d, J=3.6 Hz, 1H), 7.06 (d, J=3.6 Hz, 1H), 3.91 (s, 4H), 3.90 (s, 4H). LC-MS (ESI): Calculated mass: 343.0; Observed mass: 344.3 (RT: 1.21 min).

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