Reacción #220206

Ecuación de reacción

lithium aluminum hydride

4-[4-((R)-1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester

water

sodium hydroxide

water

→

title compound

{4-[4-((R)-1-Phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture heated
2. 2
   Temperaturato reflux for 1 h
3. 3
   TemperaturaThe mixture is cooled in an ice bath
4. 4
   OtroThe solid aluminum complex is removed by filtration (Hyflo Super Cel®; Fluka, Buchs, Switzerland)
5. 5
   Secadothe filtrate dried over sodium sulfate
6. 6
   Otroevaporated
7. 7
   Filtraciónfiltered
8. 8
   Otrodried

Procedimiento

570 mg (15 mmol) lithium aluminum hydride are suspended in 150 ml dry THF at RT. 1.23 g (3 mmol) 4-[4-((R)-1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester are added and the mixture heated to reflux for 1 h. The mixture is cooled in an ice bath and treated sequentially with water (0.57 ml), 15% sodium hydroxide solution (0.57 ml) and water (1.71 ml). The solid aluminum complex is removed by filtration (Hyflo Super Cel®; Fluka, Buchs, Switzerland), the filtrate dried over sodium sulfate evaporated. The residue is suspended in water, filtered and dried to give the title compound; m.p.>300° C.; Rf (dichloromethane/ethanol 9:1 plus 1% conc. ammonia)=0.43; HPLC tR=8.71 min.

Fuente