N,N,N',N'-Tetramethylethylenediamine → HCID 86725296, compound

Participants

Reaction Steps

In a sealed tube filled with argon, a mixture of ethyl 5-(2-amino-5-iodopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylate (612 mg, 1.0 mmol), Pd(PPh3)2Cl2 (70 mg, 0.1 mmol), CuI (19 mg, 0.1 mmol), ethynyl(trimethyl)silane (0.415 mL, 3 mmol) and triethylamine (10 mmol) in degassed ACN (10 mL) was stirred at room temperature overnight. To the reaction mixture was added N,N,N′,N′-tetramethylethylenediamine (0.3 mL, 2 mmol) and the reaction mixture stirred at the same temperature for 15 min. The solvent was evaporated under vacuum and the residue purified by flash chromatography (hexane/EtOAc 8/2) to obtain the title compound (495 mg, 85%).

Provenance & Evidence