Trimethylsilylacetylene → HCID 67163888, compound

Participants

Reaction Steps

To a suspension of (2R,3S,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(5-iodo-4-phenethyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-tetrahydrofuran-3-yl acetate 9 obtained from example 132, step d) (0.36 g, 0.578 mmol), CuI (0.022 g, 0.0116 mmol), Pd(PPh3)2Cl2 (0.040 g, 0.0570 mmol) and DIPEA (0.20 mL, 1.15 mmol) in DMF was added ethynyltrimethylsilane (0.230 g, 2.34 mmol). The mixture was stirred at r.t. for 12 h. The reaction mixture was diluted with EtOAc. The organic layer was washed with H2O, dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography (0 to 25% EtOAc/hexanes) to give the title compound (0.305 g, 58%).

Provenance & Evidence