LY-3009120

1454682-74-6

1454682-77-9

1454682-72-4

GENERAL PROCEDURE: 1-(3,3-dimethylbutyl)-3-(2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (25.9 g, 68.5 mmol), 7-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-6-yl trifluoromethanesulfonate (22.09 g 68.5 mmol) and sodium bicarbonate (17.28 g, 206 mmol) were dissolved in a solvent mixture of 1,4-dioxane (500 mL) and water (125 mL) and bubbled under argon protection for 20 min. Tetrakis(triphenylphosphine)palladium (3.96 g, 3.43 mmol) was added and the reaction was heated at 50 °C under argon atmosphere. Subsequently 7-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-6-yl trifluoromethanesulfonate (300 mg, 0.55 mmol) was added by supplementation and heating was continued at 50 °C overnight. After completion of the reaction, the mixture was cooled to room temperature, the solid was collected by filtration and washed sequentially with water and ether. The resulting solid was treated with acetonitrile (50 mL) and stirred at 80 °C for 30 min, the solid was again collected by filtration, washed with acetonitrile and dried in vacuum at 80 °C to give a light yellow solid. The solid was further treated with methanol (50 mL), heated at 80 °C for 1 h. After cooling to room temperature, the solid was filtered, washed with methanol (20 mL) and dried under vacuum to afford the target product 1-(3,3-dimethylbutyl)-3-(2-fluoro-4-methyl-5-(7-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (22.5 g, yield 77%), as a light yellow solid. Mass spectrum (m/z): 425.2 (M + 1).