3-Aminopyridine → 2-(2-(2-(5-Methyl-2-(pyridin-3-ylamino)pyrimidin-4-yl)ethyl)phenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-(2-(2-chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide (K6) (0.050 g, 0.17 mmol), 3-aminopyridine (0.019 g, 0.21 mmol), Pd(OAc)2 (0.8 mg, 0.003 mmol), Cs2CO3 (0.169 g, 0.518 mmol) and Xantphos (4 mg, 0.007 mmol) in 1,4-dioxane (1 mL) was heated under microwave irradiation at 150° C. for 10 minutes. Water (30 mL) was added and the resulting suspension was sonicated for 1 minute. The precipitate was collected by filtration then adsorbed onto silica gel and purified by silica gel column chromatography (CombiFlash Rf, 12 g SiO2 cartridge, 0-10% MeOH in DCM) to give the title compound 24 as a light pink solid (6 mg, 10%); 1H NMR (300 MHz, d4-MeOH) δ 8.87 (s, 1H), 8.26 (d, J=7.4 Hz, 1H), 8.16 (s, 1H), 8.10 (s, 1H), 7.34 (dd, J=8.1, 4.6 Hz, 1H), 7.23-7.27 (m, 1H), 7.16-7.20 (m, 3H), 3.65 (s, 2H), 3.12-3.17 (m, 2H), 2.97-3.02 (m, 2H), 2.12 (s, 3H). LCMS-B: rt 4.649 min; m/z 348 [M+H]+.

Provenance & Evidence