Water → 5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]-N-(pyridin-4-ylmethyl)oxazol-2-amine

Participants

Reaction Steps

A solution of [6-(2-chloro-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (50 mg, 0.174 mmol) in iPrOH (5 ml) was treated with 4-aminomethylpyridine (53 μl) and heated to reflux for 40 h. The cooled mixture was treated with water and extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on Al2O3 (Brockman grade III, 7% H2O), eluting with 2% EtOH in DCM. Precipitation from DCM with n-pentane afforded the title compound as pale yellow solid (34 mg, 55%). 1H NMR (300 MHz, DMSO-d6) δ 9.61 (s, 1H), 8.52 (d, J=4.6 Hz, 2H), 8.25 (t, J=5.8 Hz, 1H), 8.08 (d, J=5.0 Hz, 1H), 7.73 (s, 1H), 7.64 (t, J=7.9 Hz, 1H), 7.47 (d, J=8.3 Hz, 1H), 7.36 (d, J=4.9 Hz, 2H), 7.29 (s, 1H), 6.92 (d, J=7.6 Hz, 1H), 6.73 (d, J=5.0 Hz, 1H), 4.49 (d, J=5.7 Hz, 2H), 2.29 (s, 3H). (ESI+) m/z 359 (M+H)+.

Provenance & Evidence