Triethylamine → HCID 86712625, compound

Participants

Reaction Conditions

Reaction Steps

PPh3 (31 mg, 0.12 mmol), PdCl2(PPh3)2 (84 mg, 0.12 mmol), Et3N (0.67 mL, 4.8 mmol) and methyl 2-(2-ethynylphenyl)acetate (K1) (0.25 g, 1.4 mmol) were added to a solution of 2,4-dichloro-5-methylpyrimidine (0.20 g, 1.2 mmol) in anhydrous DMF (5.0 mL). The solution was degassed with nitrogen for 10 minutes before the addition of CuI (23 mg, 0.12 mmol). The resulting mixture was heated under microwave irradiation at 120° C. for 15 minutes then diluted with EtOAc (30 mL) and filtered through Celite. The filtrate was evaporated under reduced pressure and the resulting residue adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-35% EtOAc in petroleum benzine 40-60° C.) to give the title compound K7 as a yellow solid (0.28 g, 78%); 1H NMR (400 MHz, CDCl3) δ 8.49 (s, 1H), 7.66 (d, J=7.7 Hz, 1H), 7.46-7.40 (m, 1H), 7.39-7.31 (m, 2H), 3.93 (s, 2H), 3.71 (s, 3H), 2.45 (s, 3H). LCMS-A: rt 5.993 min; m/z 301 [M+H]+.

Provenance & Evidence