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With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; toluene; at -78℃; for 1h;Inert atmosphere;
Into a 1 0-L 4-neck round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 5-bromo-2-iodopyrimidine (590 g, 2.07 mol) in THE (3 L). This was followed by dropwise addition of 1 M solution of dimethyl zinc (3.11 L, 3.11 mol) with stirring at 0°C. To this was added Pd(PPh3)4 (120 g, 104 mmol). The resulting solution was stirred for 3 h at 0°C, then quenched by the addition of 600 mL of aqueous NH4C1. The resultingsolution was extracted with 2 x 1.5 L of ethyl acetate. The organic extracts were combined, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was applied onto a silica gel colunm and eluted with ethyl acetate/petroleum ether (1:50) to provide 5-bromo-2-methylpyrimidine. Into a 1 0-L 4-neck round-bottom flask purged and maintained with an inert atmosphereof nitrogen was placed a solution of 5-bromo-2-methylpyrimidine (184 g, 1.06 mol) and B(iPrO) 3 (240 g, 1.28 mol) in THE/toluene (3/3 L). This was followed by the dropwise addition of a 2.5 M solution of n-BuLi (510 mL, 1.28 mol) with stirring at -78°C. The resulting solution was stirred for 1 hat -78°C, then quenched by the addition of 200 nit of aqueous NH4CI. The organic phase was dried and concentrated under vacuum. The aqueous phase was adjusted to pH4 with AcOH. The solid was collected by filtration and dried in an oven under reduced pressure providing (2-methylpyrimidin-5 -yl)boronic acid.
With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; toluene; at -78℃; for 1h;Inert atmosphere;
Into a 10-L 4-neck round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 5-bromo-2-methylpyrimidine (184 g, 1.06 mol) and B (i-PrO)3(240 g, 1.28 mol) in THF/toluene (3/3 L) . This was followed by the dropwise addition of a 2.5 M solution of n-BuLi (510 mL, 1.28 mol) with stirring at -78 . The resulting solution was stirred for 1 h at -78 , then quenched by the addition of 200 mL of aqueous NH4Cl. The organic phase was dried and concentrated under vacuum. The aqueous phase was adjusted to pH 4 with AcOH. The solid was collected by filtration and dried in an oven under reduced pressure providing (2-methylpyrimidin-5-yl) boronic acid.
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