Cesium carbonate → 2-(3-(3-Chloropyrazin-2-yl)azetidin-1-yl)quinazoline

Participants

Reaction Conditions

Reaction Steps

2-(Azetidin-3-yl)-3-chloropyrazine hydrochloride (1.50 g, 7.28 mmol), 2-chloroquinazoline (1.20 g, 7.28 mmol, Parkway Scientific), and cesium carbonate (5.22 g, 16.0 mmol, Fluka) were mixed in DMF (30 mL) in a round bottom flask under a nitrogen atmosphere. The mixture was stirred at 110° C. for 17 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (2×). The combined organic extracts were washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude mixture was purified via silica gel flash column chromatography eluting with 0% to 100% EtOAc in hexanes to give 1.02 g (47%) of a yellow amorphous solid. 1H NMR (400 MHz, chloroFORM-d) δ ppm 4.41-4.50 (m, 1 H) 4.58-4.63 (m, 2 H) 4.65-4.72 (m, 2 H) 7.22-7.28 (m, 1 H) 7.61-7.72 (m, 3 H) 8.28 (d, J=2.35 Hz, 1 H) 8.51 (d, J=2.35 Hz, 1 H) 9.04 (s, 1 H). m/z=298 (M+1).

Provenance & Evidence