Potassium Carbonate → 2-Chloro-5-(4-(difluoromethoxy)phenyl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-chloropyrimidine 16 (7.7 mmol) in 1,4-dioxane (1.5 mL) is added 2-(4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 15 (8.9 mmol), 1.8M K2CO3 (16.2 mmol) and Pd(PPh3)4 (0.38 mmol). The reaction is evacuated and backfilled with nitrogen twice then heated at 150° C. for 10 min in a microwave. After this time the reaction mixture is diluted with a saturated solution of NH4Cl and extracted with DCM (3×50 mL). The organic layer is washed with brine, dried over Na2SO4 and concentrated. Purification by short silica gel chromatography using hexane:EtOAc=3:1 as eluant affords 2-chloro-5-(4-(difluoromethoxy)phenyl)pyrimidine 17. 1H NMR (400 MHz, CDCl3) δ 8.73 (s, 2H), 7.47-7.52 (m, 2H), 7.20-7.24 (m, 2H), 6.52 (t, J=72 Hz, 1H). MS (m/z) (M+1)+: 257.0.

Provenance & Evidence