Chlorotrimethylsilane → 1-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)cyclohexanol

Participants

Reaction Steps

7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (1.20 g, 5.63 mmol) was dissolved in THF (25 mL) under argon at room temperature. Chlorotrimethylsilane (1.43 mL, 11.27 mmol) was added, and the mixture was stirred at room temperature for 3 h. Then, it was cooled to 0° C., 2-propyl magnesium chloride (11.8 mL of a 2.0 M solution in THF, 23.7 mmol) was added, and stirring was maintained for another 3 h while the reaction mixture was allowed to warm to room temperature. Then, cyclohexanone (0.88 mL, 8.45 mmol) was added, and stirring was continued for 16 h. The reaction was quenched with a mixture (1:1) of concentrated aqueous ammonium chloride solution and ice until the pH reached 6-7. The mixture was extracted with two portions of ethyl acetate, and the combined organic extracts were dried over anhydrous sodium carbonate and concentrated to dryness. The product thus obtained was used without further purification (purity 68% by HPLC). Yield: 1.87 g (97% of th.).

Provenance & Evidence