Potassium Carbonate → (S)-tert-butyl 4-(2-(2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholino)pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate

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 500 mg (1.09 mmol) was dissolved in dimethoxymethane 8 ml, and then tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate 406 mg (1.31 mol) was added. Potassium carbonate 453 mg (3.28 mmol) was dissolved in distilled water 2 ml, which was then added to the reaction solution. PdCl2(dppf)2 45 mg (0.0547 mmol) was added, and the mixture was purged with N2 (g), followed by stirring at 80° C. for 2 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. 3% MeOH/MC chromatography gave a product 478 mg (78%).

Provenance & Evidence