A solution of tert-butyl 4-[(2-chloropyrimidin-4-yl)oxy]piperidine-1-carboxylate (62.8 mg, 0.2 mmol) and 5-methylbiphenyl-3-amine (36.6 mg, 0.2 mmol) in 0.1 M 1:1 TsOH:dioxane (2.0 mL) was heated to 100° C. overnight. Upon cooling to room temperature, the reaction mixture was concentrated in vacuo. The resulting light yellow solid was triturated in 1:1 dichloromethane:diethyl ether (10 mL). The solid was removed by filtration then dried under vacuum to provide N-(5-methylbiphenyl-3-yl)-4-(piperidin-4-yloxy)pyrimidin-2-amine as a tosylate salt as a light yellow solid. MS ESI calc'd. for C22H25N4O [M+H]+ 361, found 362. 1H NMR (400 MHz, DMSO-d6): δ 10.17 (s, 1H); 8.68 (s, 2H); 8.29 (d, J=6.4 Hz, 1H); 7.76 (s, 1H); 7.63 (d, J=7.9 Hz, 1H); 7.61-7.26 (m, 1H); 7.21 (s, 1H); 7.12 (d, J=8.1 Hz, 2H); 6.43 (d, J=6.4 Hz, 1H); 5.26 (s, 1H); 3.19 (s, 2H); 2.97 (s, 2H); 2.29 (s, 2H); 2.14 (s, 2H); 1.95 (s, 3H).
