反应详情

温度

0 °C

A solution of tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate (0.59 g, 1.519 mmol, Example #3 Step E) in DMF (5 mL) was added dropwise to a suspension of NaH (60% dispersion in mineral oil, 0.058 g, 1.45 mmol) in DMF (5 mL), at about 0° C. The resulting mixture was stirred at about 0° C. for about 30 min and then added dropwise to a solution of 2-bromo-1-(4-(dibenzylamino)-2-methylcyclopentyl)ethanone (0.73 g, 1.8 mmol) in DMF (10 mL) at about 0° C. The resulting mixture was stirred at about 0° C. for about 1 h and the solvent was removed under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc (100 mL each). The organic phase was separated, dried over anhydrous MgSO4 and concd under reduced pressure to yield tert-butyl 2-(4-(dibenzylamino)-2-methylcyclopentyl)-2-oxoethyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate (1.04 g, 97%) as a yellow amorphous solid: LC/MS (Table 1, Method a) Rt=3.30 min; MS m/z 708 (M+H)+.

1. stirringThe resulting mixture was stirred at about 0° C. for about 1 h
2. customthe solvent was removed under reduced pressure
3. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc (100 mL each)
4. customThe organic phase was separated
5. dry with materialdried over anhydrous MgSO4 and concd under reduced pressure