Potassium Acetate → Tert-butyl 4-(1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-fluoropyridin-3-yl)ethyl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.300 g, 0.780 mmol) and 5-(1-(4-(tert-butoxycarbonyl)piperazin-1-yl)ethyl)-2-fluoropyridin-3-ylboronic acid (0.385 g, 1.091 mmol) in dioxane (3 mL). Then A-Phos (0.055 g, 0.078 mmol), potassium acetate (0.230 g, 2.339 mmol) and water (0.5 mL) were added into the reaction mixture. The reaction mixture was stirred and heated in a CEM Explorer Microwave at 120° C. for 10 min (120 watts, Powermax feature on). The mixture was diluted with dichloromethane (10 mL), water (10 mL) and brine (5 mL). The organic layer was collected by extracting with dichloromethane (3×10 mL). The combined organic extracts were dried (magnesium sulfate), filtered and concentrated in vacuo to give the crude material as tan oil. The crude material was adsorbed onto silica gel and purified by chromatography through a silica-gel column (40 g) eluting with 100% ethyl acetate to give tert-butyl 4-(1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-fluoropyridin-3-yl)ethyl)piperazine-1-carboxylate (0.513 g, 0.780 mmol, 100% yield) as a tan solid. 1H NMR (400 MHz, CDCl3) δ 8.19-8.32 (m, 1H) 7.91 (d, J=8.02 Hz, 1H) 7.22 (dd, J=8.61, 2.93 Hz, 4H) 6.83-6.97 (m, 4H) 4.82 (d, J=9.39 Hz, 4H) 3.76-3.83 (m, 6H) 3.67-3.71 (m, 3H) 3.40 (s, 4H) 3.01 (s, 1H) 2.55 (s, 3H) 2.45 (s, 2H) 2.37 (s, 2H) 2.04-2.07 (m, 3H) 1.38-1.53 (m, 9H). m/z (ESI, +ve ion) 658.3 (M+H)+.

Provenance & Evidence