Reacción #11464

Ecuación de reacción

tert-butyl 2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethylcarbamate

triethyl orthoacetate

pyridine hydrochloride

toluene

→

tert-butyl 2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethylcarbamate

Rendimiento 100.0%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux for 30 minutes
3. 3
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
4. 4
   Otroto provide a brown oil
5. 5
   Lavadowashed with water (2×500 mL)
6. 6
   Extracciónextracted with ethyl acetate (2×500 mL)
7. 7
   LavadoThe combined organics were washed with brine
8. 8
   Secadodried over magnesium sulfate
9. 9
   Concentraciónconcentrated under reduced pressure

Procedimiento

A mixture of tert-butyl 2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethylcarbamate (43.7 g, 117 mmol), triethyl orthoacetate (22.6 mL, 123 mmol), pyridine hydrochloride (4.4 g) and toluene (440 mL) was heated at reflux for 30 minutes. The reaction mixture was concentrated under reduced pressure to provide a brown oil. The oil was dissolved in ethyl acetate (1 L) and washed with water (2×500 mL). The aqueous washes were combined and extracted with ethyl acetate (2×500 mL). The combined organics were washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure to provide 46.4 g of tert-butyl 2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethylcarbamate as a white solid, m.p. 180–182° C.

Fuente