Cesium fluoride → HCID 67509209, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-chloro-4-(3-methylpyridin-2-yl)-2-(methylsulfonyl)pyrimidine and 5-chloro-4-(3-methylpyridin-2-yl)-2-(methylsulfinyl)pyrimidine (300 mg, 1.05 mmol) in DMSO (15 mL) was added 4-(methylsulfonylmethyl)piperidine (440 mg, 1.65 mmol) and CsF (640 mg, 4.2 mmol). The resulting mixture was heated at 100° C. at microwave for 30 min. TLC (CH2Cl2:MeOH=10:1) indicated that the reaction was complete. The mixture was then treated with EtOAc (50 mL) and H2O (50 mL). The layers were separated and the aqueous layer was then extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and filtered. The filtrate was concentrated and the residue was purified via prep. HPLC to give title compound (183 mg, 46%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.47-8.48 (d, 1H), 8.28 (s, 1H), 7.55-7.56 (dd, 1H), 7.20-7.24 (m, 1H), 4.66-4.69 (d, 1H), 2.88-2.92 (m, 7H), 2.30-2.34 (m, 1H), 2.18 (s, 3H), 1.94-1.97 (m, 2 H), 1.26-1.37 (m, 2H); m/z for C17H21ClN4O2S 381.4 (M+H)+.

Provenance & Evidence