Ammonia → HCID 73776648, compound

Participants

Reaction Steps

(S)-2-(1-((5-(4-Fluoro-2-methoxyphenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (65 mg, 0.10 mmol) was dissolved in 1.3 ml dichloromethane and the reaction mixture was cooled at 0aC. Boron tribromide (1M in dichloromethane, 1 mL, 1.02 mmol) was added dropwise and the reaction mixture was stirred overnight. The reaction mixture was poured into a 4% sodium bicarbonate solution and extracted twice with dichloromethane. The organics were combined, dried, filtered and concentrated under reduced pressure. The white solid formed was re-dissolved in 650 μl anhydrous methanol and ammonia solution (7M in methanol, 1.3 ml, 9.1 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and then concentrated to dryness, suspended in water and extracted twice with ethyl acetate. The organics were combined, dried over sodium sulphate, filtered and evaporated under reduced pressure. The crude was purified using SP1® Purification System (0% to 10%, hexane-ethyl acetate) to obtain 27 mg (53% yield) of the title compound as a white solid. Purity 96%.

Provenance & Evidence