Potassium Carbonate → HCID 71730950, compound

Participants

Reaction Conditions

Reaction Steps

Combine 1-(2,4-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(3,3-dimethylbutyl)urea (3.90 g, 10.19 mmol), 6-bromo-N,7-dimethylpyrido[2,3-d]pyrimidin-2-amine (2.58 g, 10.19 mmol) and K2CO3 (4.23 g, 30.6 mmol) in dioxane (68 mL) and H2O (17 mL) and sparge with argon. Treat with tetrakis(triphenylphosphine)palladium (0.589 g, 0.510 mmol) and heat at 85° C. overnight. Cool the mixture to RT, dilute with EtOAc, filter through diatomaceous earth, and rinse well with EtOAc. Combine filtrates and wash with water (3×) and brine (1×), dry over Na2SO4, and concentrate to dryness. Treat the residue with acetonitrile and sonicate until solids precipitate. Heat the suspension at 80° C. for 2.5 h, cool to RT and collect the solids by filtration. Re-suspend solid in MeCN, heat at 80° C. for 1 h and collect by filtration. Concentrate filtrates to dryness and purify by silica gel chromatography (EtOAc/Hex, then EtOAc/MeOH/NH4OH). Treat the purified material with MeCN, sonicate, collect solids via filtration, rinsed with MeCN and dry in vacuo. Combine the crops of solids to provide title compound (2.05 g, 47%) as a pale tan solid. MS (ESI) m/z: 429.2 (M+H+).

Provenance & Evidence