Acetonitrile → HCID 56971567, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of cis-4-(4-chloro-5-(2-methylpyridin-4-yl)pyrimidin-2-yl)-2,6-dimethylmorpholine (0.100 g, 0.314 mmol), o-tolylboronic acid (0.064 g, 0.471 mmol) and potassium carbonate (0.138 g, 1 mmol) in 1,4-dioxane (3 mL) and water (0.5 mL) stirred in air at 20° C. was added solid tetrakis(triphenylphosphine)palladium(0) (0.058 g, 0.0500 mmol). The reaction mixture was stirred under nitrogen at 100° C. overnight. The reaction mixture was allowed to cool to room temperature, diluted with water and extracted with ethyl acetate (×3). The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated under reduced pressure. The crude product was purified by pre-HPLC, (Gilson GX-281; Shimadzu 15 um 250*19 mm; A:10 mMol NH4HCO3/Water B: CH3CN; 0-7 min 85-95%, 7-14 min 95%; 214 nm; 30 mL/min) to obtain the title compound (35.4 mg, 0.095 mmol, 30.1% yield). LC/MS [M+H]+=375; 1H NMR (400 MHz, CDCl3): δ 8.41 (1H, s), 8.27-8.25 (1H, s), 7.29-7.25 (1H, m), 7.17-7.14 (2H, m), 7.10-7.09 (1H, m), 6.81 (1H, s), 6.69-6.67 (1H, d), 4.69-4.65 (2H, d), 3.72-3.63 (2H, m), 2.69-2.63 (2H, m), 2.43 (3H, s), 2.07 (3H, s), 1.27-1.26 (6H, d).

Provenance & Evidence