Methyl iodide → HCID 86694685, compound

Participants

Reaction Conditions

Reaction Steps

Into a 2 L 3-necked round-bottom flask under nitrogen was placed THF (800 mL), followed by the addition of NaH (10.4 g, 260 mmol, 1.50 equiv., 60% suspension) in several batches at 0° C. over 10 min. To this suspension was added a solution of 3-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazol-5-yl]oxetan-3-ol (63.0 g, 173.3 mmol, 1.0 equiv.) in THF (300 mL), dropwise with stirring at 0° C. over 30 min. The resulting solution was stirred at 0° C. for 30 min. To the mixture was added a solution of CS2 (19.7 g, 259.21 mmol, 1.50 equiv.) in THF (100 mL), dropwise with stirring at 0° C. over 20 min. The resulting solution was stirred at 0° C. for 1 h. To the mixture was added a solution of iodomethane (37.0 g, 260.7 mmol, 1.5 equiv.) in THF (100 mL), dropwise with stirring at 0° C. over 10 min. The resulting solution was stirred at 0° C. for 1 h, then quenched by the addition of 300 mL of satd. aq. NH4Cl, concentrated in vacuo, diluted with 1 L of water and extracted with 3×1 L of EtOAc. The combined organic layers were washed with 2×1 L of water and 2×500 mL of brine, dried (Na2SO4) and concentrated in vacuo to afford ([3-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-[[2-(trimethylsilyl)ethoxy]-methyl]-1H-pyrazol-5-yl]oxetan-3-yl]oxy)(methylsulfanyl)methanethione (80.0 g, 97% yield) as a yellow oil.

Provenance & Evidence