6-Dimethylaminopyridine-3-boronic acid pinacol ester

To a solution of 5-bromo-2-(NN-dimethylamino)pyridine (8.5 g, 42.3 mmol) and 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2, 2'-bi(1, 3, 2-dioxaborolane) (12.9 g, 50.7 mmol) in dioxane (10 mL) was added KOAc (8.3 g, 84.6 mmol) and Pd(dppf)Cl2 (1.55 g, 2.1 mmol) at 25 °C under N2. The mixture was heated to 100 °C and stirred at this temperature for 12 hours. LCMS showed that the reaction was complete. The mixture was filtered and concentrated under reduced pressure to give a residue which was purified by silica gel column chromatography (petroleum ether / ethyl acetate=50/1 to 3/1) to give 2-(2-(N, N-dimethylamino)pyrid-5-yl-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane (8 g, 32.2 mmol, 76percent yield) as a yellow solid 1H NMR 400 MHz CDCl3 = 8.53 (s, 1H), 7.75-7.78 (d, 1H), 6.43-6.45 (d, 1H), 3.09 (s, 6H), 1.22-1.30 (m, 12H). ESI-MS (m/z): 249.2 (M+H)+WX297-2 (836.83 mg, 3.36 mmol), dioxane (5 mL) and water (1.5 mL) were added into a pre-dried 50 mL single-necked flask, and then K2CO3 (1.16 g, 8.41 mmol) and WX297-3 (834.81 mg, 3.36 mmol) were added, followed by addition of tetrakis(triphenylphosphine)palladium (388.78 mg, 336.44 mumol) under nitrogen atmosphere. The reaction mixture was stirred at 100C for 12 hours. After the reaction mixture was quenched with water (5 mL), the aqueous phase was extracted with ethyl acetate (3*10 mL). The organic phase was dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under reduced pressure to remove the solvent to give a crude product. The crude product was subjected to column chromatography to give WX297-4.To a solution of 2-(2-(N, N-dimethylamino)pyrid-5-yl-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane (8 g, 32.2 mmol) and 2, 4, 5-trichloropyrimidine (7.1 g, 38.7 mmol) in dioxane (80 mL) and H2O (20 mL) was added Na2CO3 (10.3 g, 96.7 mmol) and Pd(dppf)Cl2 (1.2 g, 1.6 mmol) at 25 C under N2. The mixture was heated to 100 C and stirred at this temperature for 12 hours. LCMS showed that the reaction was complete. The mixture was filtered and concentrated under reduced pressure to give a residue, which was purified by prep-HPLC (column: Phenomenex luna C18 250*80mm*10 um; mobile phase: [water (0.1%TFA)-ACN]; B%: 10%-40%, 20min). 2, 5-dichloro-4-(6-(N, N-dimethylamino)pyrid-3-yl)pyrimidine (3.5 g, 13 mmol, 40% yield) was obtained as a light yellow solid. ESI-MS (m/z): 269.1 (M+H)+.

Molecular Weight:248.13
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:248.1696081
Monoisotopic Mass:248.1696081
Topological Polar Surface Area:34.6
Heavy Atom Count:18
Complexity:291
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes