Reacción #73226
ord-fb0dff9cd6a1457291fa4630b5fcb1f3
Ecuación de reacción
Reactantes
Reactivos
Disolventes
Condiciones de reacción
Tratamiento posterior
- 1Temperaturato reflux overnight
- 2OtroThe solvent was removed by rotary evaporation
- 3Otroto give a greenish orange oil/glass
- 4ExtracciónThe aqueous phase was extracted with ethyl acetate
- 5LavadoThe organic layers were washed with brine
- 6Otroreduced by rotary evaporation
- 7Otroto give an oil/glass residue
- 8OtroThe solvent was removed by rotary evaporation
- 9Otroto give a pale orange foam/solid
- 10OtroThe crude was chromatographed with 0-7% MeOH/DCM, 0-0.7% NH4OH
Procedimiento
A solution of 4,4,4-trifluoro-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile (3.1 g, 0.0071 mol) from Step 1 in THF (35 mL, 0.43 mol) and 3.0 M HCl in water (35 mL) was heated to reflux overnight. The solvent was removed by rotary evaporation to give a greenish orange oil/glass. The oil was stirred with ethyl acetate and sat. NaHCO3 (50 mL). The aqueous phase was extracted with ethyl acetate. The organic layers were washed with brine and reduced by rotary evaporation to give an oil/glass residue. The residue was stirred in ethanol (20 mL, 0.3 mol) and 8.0 M ammonium hydroxide in water (10 mL) over a weekend. The solvent was removed by rotary evaporation to give a pale orange foam/solid. The crude was chromatographed with 0-7% MeOH/DCM, 0-0.7% NH4OH to give 3 g of a pale orange paste/solid. The solid was recrystallized from EtOH to give 1.6 g of an off-white crystals (74% yield).