Reacción #657328

Ecuación de reacción

water

acetyl chloride

4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amine

triethylamine

→

N-acetyl-N-[4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide

Rendimiento 37.0%

Disolventes

tetrahydrofurane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with dichloromethane (3×50 mL)
2. 2
   LavadoThe combined organic layers are washed with a saturated solution of NaHCO3, brine
3. 3
   Secadodried over anhydrous magnesium sulphate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe crude material is purified by column chromatography

Procedimiento

To a solution of 4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amine (420 mg, 1.46 mmol, 1 eq) in 20 mL of tetrahydrofurane is added triethylamine (0.82 mL, 5.85 mmol, 4 eq) and then acetyl chloride (234 mg, 2.92 mmol, 2 eq). The mixture is stirred overnight at room temperature and then poured into water and extracted with dichloromethane (3×50 mL). The combined organic layers are washed with a saturated solution of NaHCO3, brine, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material is purified by column chromatography using silica gel in heptane and ethyl acetate (1:0 to 0:1) as eluent and 0.23 g (37%) of N-acetyl-N-[4-(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide are obtained as a yellow solid.

Fuente