Cesium carbonate → (3R)-tert-butyl 3-(6-methoxy-2-morpholino-5-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)pyrimidin-4-ylamino)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 5-(trifluoromethyl)-1,3-benzothiazole (100 mg, 0.49 mmol, 1.80 equiv) in N,N-dimethylformamide (5.0 mL), tert-butyl 3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (140.2 mg, 0.27 mmol, 1.00 equiv), Cesium Carbonate (534.3 mg, 6.00 equiv), Tetrakis(triphenylphosphine)palladium (57.8 mg, 0.05 mmol, 0.18 equiv), and Copper (I) iodide (9.5 mg, 0.05 mmol, 0.18 equiv). The resulting mixture was heated for 2.5 h at 85° C. in an oil bath, cooled down, quenched by the addition of 15 mL of water and then extracted with ethyl acetate (4×15 mL). The combined organic layers were washed with brine (20 mL) and dried over anhydrous sodium sulfate. After filtration and concentration under reducing pressure, the residue was purified by chromatography on a silica gel column eluting with petroleum ether/ethyl acetate (10:1-3:1) to afford the title compound as a gray white solid. MS m/z [M+H]+ (ESI): 595

Provenance & Evidence