Reacción #88955

Ecuación de reacción

chlorotriisopropylsilane

Intermediate 74e

{5-Amino-3-tert-butyl-1′-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1′H-[1,4′]bipyrazolyl-3′-yl}-methanol

imidazole

→

title compound

Rendimiento 79.0%

3-tert-Butyl-1′-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-3′-triisopropylsilanyloxymethyl-1′H-[1,4′]bipyrazolyl-5-ylamine

Rendimiento 79.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was evaporated in vacuo
2. 2
   Otrothe residue was partitioned between EtOAc and water
3. 3
   ExtracciónThe aqueous layer was then extracted with EtOAc (2×)
4. 4
   LavadoThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine
5. 5
   Secadodried (Na2SO4)
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated in vacuo
8. 8
   OtroThe residue was purified by FCC

Procedimiento

A solution of Intermediate 74e (0.39 g, 1.10 mmol) in DMF (3.9 mL) was treated with imidazole (0.18 g, 2.7 mmol) then chlorotriisopropylsilane (0.28 mL, 1.3 mmol) and the mixture was stirred at RT for 22 h. The mixture was evaporated in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (2×). The combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-4% MeOH in DCM, to give the title compound (0.44 g, 79%). LCMS (Method 3): Rt 4.20 min, m/z 520 [MH+].

Fuente