Réaction #657327

Équation de réaction

water

4-(2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amine

triethylamine

Triethylamine

acetyl chloride

acetyl chloride

→

N-[4-(2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide

Rendement 12.0%

Solvants

tetrahydrofurane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture is stirred overnight at room temperature
2. 2
   Extractionextracted with dichloromethane (3×50 mL)
3. 3
   LavageThe combined organic layers are washed with a saturated solution of NaHCO3, brine
4. 4
   Séchagedried over anhydrous magnesium sulphate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe crude material is purified by column chromatography

Mode opératoire

To a solution of 4-(2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-amine (29 mg, 0.1 mmol, 1 eq) in 2 mL of tetrahydrofurane is added triethylamine (0.055 mL, 0.4 mmol, 4 eq) and then acetyl chloride (0.024 mL, 0.3 mmol, 3 eq). The mixture is stirred for 4 h at room temperature. Triethylamine (0.055 mL, 0.4 mmol, 4 eq) and acetyl chloride (0.024 mL, 0.3 mmol, 3 eq) are then added. 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 4 mg (8%) of N-[4-(2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)pyridin-2-yl]acetamide are obtained as a light brown oil.

Source