Reacción #169872

Ecuación de reacción

CaCl2

Trifluoroacetic anhydride

1-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

urea hydrogen peroxide

NaHCO3

→

1-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 4-oxide

Disolventes

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with EtOAc
2. 2
   OtroThe organic layer was separated
3. 3
   Lavadowashed with water and brine
4. 4
   Secadodried over MgSO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue was purified by column chromatography (NH silica gel, eluted with 0%-100% EtOAc in hexane)

Procedimiento

Trifluoroacetic anhydride (3.92 mL) was added to a suspenstion of 1-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (4 g) and urea hydrogen peroxide (2.74 g) in EtOAc (20 mL) at 0° C. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) overnight. The mixture was neutralized with sat. NaHCO3 at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-100% EtOAc in hexane) to give 1-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 4-oxide (250 mg) as colorless crystals.

Fuente