7-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine → 5-(7-Chlorothieno[3,2-b]pyridin-2-yl)-1-(2-morpholinoethyl)pyrimidin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of the tributyltin derivative 6 (1.88 g, 4.1 mmol) (scheme 2) in toluene (39 mL) was added 5-bromo-1-(2-morpholinoethyl)pyrimidin-2(1H)-one (413, 1.29 g, 4.5 mmol) and Pd(PPh3)4 (474 mg, 0.41 mmol). The reaction mixture was stirred at 100° C. for 16 h. The mixture was filtered and the solvent was evaporated. The residue was triturated in hexanes, then triturated in EtOAc to produce title compound 414 (236 mg, 15% yield). MS (m/z): 377.0 (M+H). 1H NMR (DMSO-d6) δ (ppm): 9.18 (d, J=3.5 Hz, 1H), 8.76 (d, J=3.3 Hz, 1H), 8.64 (d, J=5.1 Hz, 1H), 8.05 (s, 1H), 7.57 (d, J=5.1 Hz, 1H), 4.06 (t, J=5.9 Hz, 2H), 3.54 (t, J=4.5 Hz, 4H), 2.64 (t, J=5.9 Hz, 2H), 2.49-2.43 (m, 4H).

Provenance & Evidence