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Part A: 2,6-Dichloro-5-fluoro-N-methyl-N-(4-pyridinylmethyl)-4-pyrimidinamine. Commercially available N-methyl-1-(4-pyridinyl)methanamine (0.305 g, 2.5 mmol) was dissolved in THF (5 ml_). To this solution was added triethylamine (0.38 ml_, 2.73 mmol), followed by 2,4,6-trichloro-5-fluoropyrimidine (0.5 g, 2.5 mmol), which was dissolved in THF (5 ml_). The reaction was left to stir for 2.5 hours. The reaction mixture was diluted with water, then extracted with ether. The organics were dried (MgSO4) and concentrated. The resulting material was purified via filtration over silica gel with a solvent mixture of 5% MeOH in 95% DCM as the mobile phase to provide 2,6-dichloro-5- fluoro-N-methyl-N-(4-pyridinylmethyl)-4-pyrimidinamine as a brown oily solid (0.3516 g, 49%). LCMS: (M+H)+ = 287.0.
5-(2,6-dichloro-5-fluoropyrimidin-4-yl)-1-methylpyridin-2(1H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
19%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 80℃; for 4h;Inert atmosphere;
A mixture of 2,4,6-trichloro-5-fluoropyrimidine (736 mg, 3.7 mmol), <strong>[1002309-52-5]1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one</strong> (860 mg, 3.7 mmol), Pd(PPh3)4 (295 mg, 0.26 mmol), K3PO4 (0.92 mL, 2 mol/L, aq) in dioxane (24 mL) was bubbled with N2 for 5 min. The mixture was stirred at 80° C. for 4 h. After the mixture was diluted with water, it was extracted with EtOAc; the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with a gradient of EtOAc [0 to 80percent] in DCM. The fractions were collected and concentrated under reduced pressure to afford the title compound (190 mg, 19percent) as a white solid. LCMS (M+H)+275.
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