Triethylamine → HCID 86712705, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-(2-ethynylphenyl)acetate (K1) (0.35 g, 2.0 mmol) in DMF (3 mL) and Et3N (0.70 mL, 5.0 mmol) was added to a mixture of 2,4-dichloro-5-methoxypyrimidine (0.30 g, 1.7 mmol), PdCl2(PPh3)2 (0.12 g, 0.17 mmol), CuI (0.032 g, 0.17 mmol) and PPh3 (0.044 g, 0.17 mmol) in DMF (3 mL). The resulting mixture was heated under microwave irradiation at 120° C. for 15 minutes, then diluted with EtOAc and passed through a plug of Celite, washing with EtOAc (50 mL). The volatiles were removed in vacuo and the residue was purified by silica gel column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-25% EtOAc in hexanes) to give the title compound A98 as a pale yellow solid (0.38 g, 72%); 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.65 (dd, J=7.6, 1.0 Hz, 1H), 7.46-7.29 (m, 3H), 4.03 (s, 3H), 3.99 (s, 2H), 3.71 (s, 3H). LCMS-A: rt 5.92 min; m/z 317.1 [M+H]+.

Provenance & Evidence