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INTERMEDIATE 59 4-(3-Iodo-lH-pyrazol-l -yl)-2-methylpyrimidine To a solution of 3-iodo-lH-pyrazole (500 mg, 2.58 mmol) in anhydrous DMSO (6 mL) was added NaH (155 mg, 3.87 mmol) at 0 C. The mixture was stirred for 30 min at 0 C, followed by the addition of 4-chloro-2-methylpyrimidine (331 mg, 2.58 mmol) in DMSO (2 mL). The resulting mixture was stirred at 90 C overnight. The mixture was cooled to room temperature, quenched with water (10 mL) and extracted EtOAc (40 mL x 3). The organic layer was collected and dried over Na2S04. The solvent was removed in vacuo to give the crude product. This was purified by flash chromatography (ISCO Combiflash, 24 g, Biotage Si column, -60 mL/min, 100% hexanes 5 min, gradient to 100% EtOAc in hexanes 15 min) to afford 4-(3-iodo-17J- pyrazol-l-yl)-2-methylpyrimidine. LCMS calc. = 286.98; found = 286.95 (M+H)+.
4-(6-fluoro-5-methylpyridin-3-yl)-2-methylpyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
67%
With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II); caesium carbonate; In 1,4-dioxane; water; at 80℃; for 1.0h;Inert atmosphere;
A stirred solution of 4-chloro-2-methylpyrimidine (100 mg, 0.778 mmol), CS2CO3 (507 mg, 1.556 mmol), <strong>[904326-92-7](6-fluoro-5-methylpyridin-3-yl)boronic acid</strong> (121 mg, 0.778 mmol) in a mixture of 1 ,4-dioxane (6 mL) and water (0.5 mL) was purged with nitrogen for 3 min. XPhos 2nd generation precatalyst (61.2 mg, 0.078 mmol) was added in one portion and the reaction mixture was heated to 80 C and stirred for 1 h. The reaction mixture was allowed to cool to room temperature. Water (20 mL) was added and the solution was extracted with EtOAc (2 x 30 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc in hexanes) to afford 4-(6-fluoro-5-methylpyridin-3-yl)-2-methylpyrimidine (115 mg, 0.521 mmol, 67% yield) as an off-white solid. LCMS (ESI) m/e 204.2 [(M+H)+, calcd for C11H11FN3, 204.1]; LC/MS retention time (method Al) to = 1.90 min.
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