Toluene → HCID 86710173, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL round bottom flask, 4-(2-chloro-6-fluoro-7-(3-(methylsulfonyl)phenyl)quinazolin-4-yl)morpholine (0.1 g, 0.0002 mol), (2-((tert-butoxycarbonyl)amino)pyrimidin-5-yl)boronic acid (0.085 g, 0.0003 mol), cesium carbonate (0.192 g, 0.0005 mol), toluene (5 mL), ethanol (5 mL) and water (2 mL) were added. The reaction vessel was degassed with N2 for 5-10 minutes. To the same reaction mixture, Pd(PPh3)2Cl2 (0.008 g, 0.000012 mol) was added and again degassed with N2 for 5-10 minutes. The reaction mixture was stirred at 75° C. for 3 hours. The reaction mixture was cooled and diluted with chloroform. The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was removed under the reduced pressure to afford the crude product. The crude product was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in n-hexane) to yield tert-butyl (5-(6-fluoro-7-(3-(methylsulfonyl)phenyl)-4-morpholinoquinazolin-2-yl)pyrimidin-2-yl)carbamate [0.06 g, 43%]. LC-MS (ESI): Calculated mass: 580.1; Observed mass [M+H]+: 581.3 (RT=1.52 min).

Provenance & Evidence