Lithium Chloride → 6-(4-(benzyloxy)-3-fluorophenyl)-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-bromo-1-phenyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one (0.075 g, 0.257 mmol), 4-(benzyloxy)-3-fluorophenylboronic acid (0.076 g, 0.308 mmol), Pd(PPh3)4 (0.015 g, 0.013 mmol) and lithium chloride (0.044 g, 1.03 mmol) in dioxane (2 mL) and 2M aqueous Na2CO3 was stirred at 100° C. for 30 minutes. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography, eluting with 10:1 CH2Cl2/EtOAc. The product was obtained (84 mg; 79%) as a pale tan solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.04 (s, 1H), 7.82 (m, 2H), 7.61 (dd, 1H), 7.50-7.31 (m, 8H), 7.25 (t, 1H), 7.14 (t, 1H), 5.21 (s, 2H), 4.20 (m, 4H). LRMS (APCI pos) m/e 414 (M+1).

Provenance & Evidence