Cesium carbonate → (2S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)pyrimidin-2-yl)morpholine

Participants

Reaction Conditions

Reaction Steps

(S)-4-(5-bromopyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine 300 mg (0.66 mmol) was dissolved in dimethoxymethane 12 ml, and 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazole 450 mg (1.39 mmol) was added. Cesium carbonate 641 mg (1.97 mmol) was dissolved in distilled water 3 ml, which was then added to the reaction solution. PdCl2(dppf)2 27 mg (0.03 mmol) was added, and the mixture was purged with N2 (g), followed by stirring at 80° C. for 4 hours. After the completion of the reaction, the reaction mixture was extracted with ethyl acetate and brine, and the organic layer was dried over Na2SO4. Prep LC with 5% MeOH/MC gave a product 290 mg (77%).

Provenance & Evidence