Potassium Iodide → (5-fluoropyridin-2-yl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone

Participants

Reaction Steps

To a stirred mixture of (4-chloroquinazolin-2-yl)(5-fluoropyridin-2-yl)methanone (244 mg, 0.85 mmol) and 5-methyl-3-aminopyrazole (99 mg, 1.02 mmol) in N,N-dimethylformamide (3 mL) were added DIEA (0.3 mL, 4.22 mmol) and potassium iodide (141 mg, 0.85 mmol) and the mixture was stirred at rt for 15 h and then at 60° C. for 2.5 h. The mixture was allowed to cool to rt, and then water was added. The precipitated solid was collected by filtration. A portion of the solid (180 mg) was purified by preparative reverse-phase HPLC eluting with 30% to 70% acetonitrile/0.05% aq HOAc to afford (5-fluoropyridin-2-yl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone (19.6 mg). 1H NMR (300 MHz, CDCl3) δ 12.19 (s, 1H), 10.65 (s, 1H), 8.72-8.69 (m, 2H), 8.26 (m, 1H), 8.00 (td, J=3 Hz, J=8.7 Hz, 1H), 7.92-7.80 (m, 2H), 7.66 (t, J=7.5 Hz, 1H), 6.34 (s, 1H), 2.16 (s, 3H); LC-MS (ESI) m/z 349 (M+H)+.

Provenance & Evidence