Hydrochloric Acid → cis-2-[2-(2,6-Dimethyl-4-morpholinyl)-5-(2-methyl-4-pyridinyl)-4-pyrimidinyl]-4-fluorobenzonitrile hydrochloride

Participants

Reaction Conditions

Reaction Steps

Sodium carbonate (166 mg, 1.568 mmol) in water (2 mL), bis(triphenylphosphine) palladium(II) chloride (11.01 mg, 0.016 mmol) and 2-cyano-5-fluorophenylboronic acid pinacol ester (155 mg, 0.627 mmol) were added to a solution of cis-4-[4-chloro-5-(2-methyl-4-pyridinyl)-2-pyrimidinyl]-2,6-dimethylmorpholine (100 mg, 0.314 mmol) in 1,2-dimethoxyethane (3 mL). The reaction mixture was heated to 100° C. for 2 hour. The reaction mixture diluted with water (5 mL) and extracted with DCM (5 mL×2). The organic extracts were combined, dried (MgSO4), filtered and the solvent was removed. The resulting residues were then purified by MDAP and fractions containing desired product were combined and evaporated to give a solid. The solid was then dissolved in methanol (2 mL) and 4M HCl in dioxane (1 mL) was added. The solvent was removed to give the title compound (50 mg). LC/MS [M+H]+=404. 1H NMR (400 MHz, d6-DMSO): δ 8.82 (1H, s), 8.56 (1H, d), 8.10-8.05 (1H, m), 7.77-7.79 (1H, m), 7.56-7.62 (1H, m), 7.45-7.39 (2H, m), 4.70-4.66 (1H, m), 3.63-3.57 (2H, m), 2.76-2.68 (2H, m), 2.64 (3H, s), 1.18 (6H, d).

Provenance & Evidence