Cesium carbonate → 2-benzyl-5-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-chloro-2-iodothieno[3,2-b]pyridine (0.030 g, 0.10 mmol; prepared according to the procedure described by Ragan, J. A. Org. Proc. Res. Dev. 2003, 7, 676) and 2-benzyl-5-(3-fluoro-4-hydroxyphenyl)pyrimidin-4(3H)-one (0.025 g, 0.084 mmol) in DMF (1 mL) was added Cs2CO3 (0.033 g, 0.10 mmol). The reaction mixture was stirred at 130° C. for 18 hours. The reaction mixture was partitioned between EtOAc and saturated aqueous NaCl. The phases were separated, and the aqueous phase was re-extracted with EtOAc (2×). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude dark yellow solid. Purification of the crude product was achieved by flash column chromatography (25:1 dichloromethane/methanol) and then by trituration with dichloromethane. The resulting solid was filtered, washed with dichloromethane, collected and dried under vacuum to yield the desired product (0.008 g, 17%) as a pale yellow solid. LRMS (ESI pos) m/e 556 (M+1).

Provenance & Evidence