4-Aminopyridine → HCID 135939044, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 2-(4-bromophenyl)-5,7-dimethoxyquinazolin-4(3H)-one) (0.200 g, 0.554 mmol), 4-aminopyridine (0.0573 g, 0.609 mmol), Pd2(dba)3 (0.0025 g, 0.0028 mmol), Xantphos (0.0018 g, 0.0031 mmol), and Cs2CO3 (0.253 g, 0.776 mmol) in 1,4-dioxane (2.22 mL) under nitrogen was heated at 105° C. for 2 days. The mixture was cooled to room temperature, diluted with EtOAc (200 mL), washed with water (3×75 mL), then brine (75 mL), dried over anhydrous Na2SO4, filtered, and the solvent was removed under vacuum. The resulting residue was purified over silica gel (12 g, EtOAc/CHCl3/MeOH/NH4OH), to provide the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 11.90 (s, 1H), 9.19 (s, 1H), 8.29 (d, J=6.29 Hz, 2H), 8.17 (d, J=8.75 Hz, 2H), 7.30 (d, J=8.75 Hz, 2H), 7.05 (d, J=6.29 Hz, 2H), 6.72 (d, J=2.26 Hz, 1H), 6.51 (d, J=2.26 Hz, 1H), 3.89 (s, 3H), 3.85 (s, 3H). MS (ESI) m/z 375 [C21H18N4O3+H]+.

Provenance & Evidence