Réaction #1896889

Équation de réaction

N-Boc-trans-1,4-cyclohexanediamine

3-(3-bromo-phenyl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine

Et3N

(2-(chloromethoxy)-ethyl)trimethylsilane

→

{4-[3-(3-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

Solvants

water

DMF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with EtOAc (3×200 mL)
2. 2
   ExtractionThe EtOAc extract
3. 3
   Séchagewas dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   AutreThe crude product was purified by chromatography (silica gel, 200-300 mesh, EtOAc)

Mode opératoire

To a solution of 3-(3-bromo-phenyl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine (from Example 38 supra) (3.0 g, 9.7 mmol), Et3N (5.4 mL, 38.8 mmol) in DMF (50 mL), (2-(chloromethoxy)-ethyl)trimethylsilane (SEM-Cl, 2.0 mL, 11.6 mmol) was added in one portion. The resultant mixture was stirred for 30 minutes at room temperature. To this solution, N-Boc-trans-1,4-cyclohexanediamine (2.48 g, 11.6 mmol) was added. The resulting mixture was stirred for one hour at room temperature. The reaction was then poured into water (200 mL) and extracted with EtOAc (3×200 mL). The EtOAc extract was dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography (silica gel, 200-300 mesh, EtOAc) to give {4-[3-(3-bromo-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester as yellow oil. (Yield 2.2 g, 37.3%).

Source