5-Methyl-2-(tributylstannyl)thiazole → 6-[2-chloro-4-(5-methylthiazol-2-yl)phenyl]-8-ethyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one

Participants

Reaction Conditions

Reaction Steps

6-(4-Bromo-2-chlorophenyl)-8-ethyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one (12, 194 mg, 0.35 mmol), 5-methyl-2-(tributylstannyl)-thiazole (171 mg, 0.44 mmol), Pd(PPh3)4 (50 mg) and toluene (15 mL) were placed in a microwave tube and oxygen was removed by a stream of argon. The reaction was heated by microwave at 140° C. for 1.5 h and was monitored by LC/MS. The reaction mixture was evaporated and the solid was extracted with chloroform (100 mL). The solids were removed and the filtrate was evaporated and purified by silica gel chromatography (CHCl3+5% MeOH). Yield 17 mg, 0.03 mmol, 8% as yellow solid. LCMS m/z 572 (M+H)+Rt 1.74 min; 1H NMR (400 MHz, CDCl3) δ ppm 8.56 (s, 1H), 8.04 (s, 1H), 7.81-7.83 (d, 1H), 7.54-7.61 (m, 4H), 7.46-7.48 (d, 1H), 7.32-7.37 (s, 1H), 6.97-7.00 (d, 2H), 4.48-4.54 (q, 2H), 3.24-3.26 (m, 4H), 2.63-2.65 (m, 4H), 2.54 (s, 3H), 2.40 (s, 3H), 1.38-1.42 (t, 3H).

Provenance & Evidence