Triphenylphosphine → 2-Furan-2-yl-6-(5-phenyl-pent-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

Participants

Reaction Steps

A solution of 6-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine (56 mg, 0.2 mmol; see Examples 1 and 2 above), pent-4-ynyl-benzene (44 mg, 0.3 mmol), Pd(PPh3)4 (26 mg, 0.03 mmol), CuI (4 mg, 0.03 mmol), PPh3 (8 mg, 0.03 mmol), and TEA (11 μL, 2.5 mmol) in DMF (5 mL) was heated (at around 105° C.) under N2 for 2 hours. The reaction was diluted with EtOAc (15 mL) and washed with brine (3×10 mL) and dried with MgSO4. The solvent was removed and the reaction purified by HPLC (C18, H2O:MeCN gradient) to afford the product as a brown solid (28 mg,). 1H NMR (400 MHz, DMSO-d6) δ 1.85 (quin, J=7.5 Hz, 2H) 2.44 (t, J 7.1 Hz, 2H), 2.74 (t, J=7.8 Hz, 2H), 6.72 (dd, J=3.4, 1.8 Hz, 1H), 7.14 (dd, J=3.5, 0.8 Hz, 1H), 7.2-7.30 (br m, 5H), 7.92 (dd, J=1.7, 0.8 Hz, 1H), 8.35 (s, 1H). MS: m/z 344 [M+H]+.

Provenance & Evidence