Dimethylformamide → HCID 135939046, compound

Participants

Reaction Steps

A mixture of 2-(4-bromophenyl)-5,7-dimethoxyquinazolin-4(3H)-one (0.200 g, 0.55 mmol), 3-aminopyridine (0.057 g, 0.61 mmol), Cs2CO3 (0.253 g, 0.776 mmol), Xantphos (0.002 g, 0.003 mmol), and Pd2(dba)3 (0.003 g, 0.003 mmol) in dioxane (2 mL) were combined in a microwave tube under nitrogen and irradiated at 300 W, 105° C. for 30 minutes. Then, DMF (1 mL) was added and the flask was irradiated for 1 hour at 300 W, 105° C. Then, the mixture was concentrated and purified by silica gel chromatography, eluting with 92:7:1 CHCl3/MeOH/concentrated NH4OH. The residue was further purified by reverse-phase HPLC, eluting with 10% to 90% CH3CN in H2O with 0.1% TFA, to afford the title compound (0.105 g, 51%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 11.83 (s, 1H), 8.82 (s, 1H), 8.44 (d, J=2.4 Hz, 1H), 8.11-8.16 (m, 3H), 7.59-7.62 (m, 1H), 7.31-7.35 (m, 1H), 7.13 (d, J=8.7 Hz, 2H), 6.68 (d, J=1.8 Hz, 1H), 6.46 (d, J=1.8 Hz, 1H), 3.88 (s, 3H), 3.83 (s, 3H). APCI MS m/z 375 [M+H]+.

Provenance & Evidence