Sodium t-butoxide → N-(2,5-di-4-morpholinylphenyl)-3-methyl-2-(2-pyridinyl)-1,8-naphthyridin-4-amine

Participants

Reaction Steps

To a stirred solution of 4-chloro-3-methyl-2-(pyridin-2-yl)-1,8-naphthyridine (48.6 mg, 0.19 mmol), 2,5-dimorpholinoaniline (50 mg, 0.19 mmol) and XPhos precatalyst (14 mg, 0.019 mmol) in toluene (4 mL) was added sodium tert-butoxide (36 mg, 0.38 mmol) and the reaction was heated at reflux for 2 h. After this time the reaction was allowed to cool to rt and partitioned between EtOAc (60 mL) and water (20 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Purification by reverse phase HPLC gave N-(2,5-di-4-morpholinylphenyl)-3-methyl-2-(2-pyridinyl)-1,8-naphthyridin-4-amine. H NMR (500 MHz, CDCl3) δ ppm 9.08 (1H, dd, J=3.9, 1.7 Hz), 8.71 (1H, br. s.), 8.26 (1H, dd, J=8.3, 1.7 Hz), 8.16 (1H, d, J=7.8 Hz), 7.88-7.96 (1H, m), 7.39 (2H, dd, J=8.3, 4.2 Hz), 7.11 (1H, d, J=8.8 Hz), 6.45 (1H, dd, J=8.7, 2.6 Hz), 5.99 (1H, d, J=2.7 Hz), 3.90 (4H, t, J=4.4 Hz), 3.66-3.77 (4H, m), 3.05 (4H, br. s.), 2.82-2.93 (4H, m), 2.51 (3H, s). Mass Spectrum (ESI) m/e=483.2 (M+1).

Provenance & Evidence