7-Chloro-2-iodothieno(3,2-b)pyridine → 2-(benzylamino)-5-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one

Participants

Reaction Steps

A mixture of 2-(benzylamino)-5-(3-fluoro-4-hydroxyphenyl)-3-methylpyrimidin-4(3H)-one (0.036 g, 0.112 mmol), 7-chloro-2-iodothieno[3,2-b]pyridine (0.030 g, 0.102 mmol; prepared according to the procedure of Ragan, J. A. Org. Proc. Res. 2003, 7, 676) and DMAP (0.025 g, 0.20 mmol) in bromobenzene (1.5 mL) under nitrogen was stirred at 150° C. for 3 days. The reaction was concentrated in vacuo to remove as much bromobenzene as possible. MeOH was added to the residue and a brown solid precipitate was filtered and discarded. The filtrate was concentrated and then purified by flash column chromatography, eluting with 20:1 CH2Cl2/MeOH. The product was obtained (15.7 mg; 27%) as a yellow solid. LRMS (APCI pos) m/e 585 (M+1).

Provenance & Evidence