Triethylamine → HCID 18186456, compound

Participants

Reaction Steps

A solution of 4-anilino-2-chloro-5-iodopyrimidine (Method 59; 662 mg, 2.0 mmol), 4-phenyl-1-butyne (260 mg, 2.0 mmol) and triethylamine (0.56 ml, 4.0 mmol) in THF (20 ml) was purged with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (25 mg) and cuprous iodide (12.5 mg) were added and the mixture was stirred for 20 hours. Insoluble material was removed by filtration and washed with diethyl ether (50 ml). The filtrate and washings were combined and concentrated, and the residue was purified by bond elute chromatography, eluting with 25% ethyl acetate in isohexane, to give the product (0.5 g). NMR (CDCl3): 2.85 (m, 2H), 2.95 (m, 2H), 7.05 (m, 2H), 7.1-7.4 (m, 7H), 7.45 (dd, 2H), 8.2 (s, 1H); MS (MH+): 334, 336.

Provenance & Evidence