Sodium Carbonate → 7-[(E)-2-(4-Chlorophenyl)vinyl]-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Participants

Reaction Steps

To a stirred solution of Intermediate 1 (100 mg, 0.231 mmol) in toluene (20 ml) and ethanol (10 ml) was added phenylboronic acid (33 mg, 0.276 mmol) and Pd[(C6H5)3P]4 (26 mg, 0.023 mmol) in) followed by sodium carbonate (Na2CO3) (48 mg, 0.461 mmol) in water (10 ml). The reaction mixture was heated to reflux for 12 h under nitrogen. The reaction mixture was allowed to cool to room temperature. The residue obtained after evaporation was partitioned between ethyl acetate (500 ml) and water (100 ml). The organic layer was washed with brine (100 ml), dried (Na2SO4) and concentrated to afford a crude product which was purified by silica gel column chromatography using 10% ethyl acetate in chloroform to give 5 g of the product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 2.19 (s, 3H), 6.85 (d, J=4.8 Hz, 1H), 7.53 (d, J=7.8 Hz, 3H), 7.77 (m, 4H), 7.88 (d, J=7.8 Hz, 1H), 8.02 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 265.31 (M−H)−.

Provenance & Evidence