Reacción #3330

Ecuación de reacción

water

2-naphthyl-acetonitrile

NaH

4-ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde

→

yellow solid

Rendimiento 82.4%

(8-Ethyl-7-imino-6-naphthalen-2-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine

Rendimiento 82.4%

Disolventes

2-ethoxyethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction heated at 110° C. for 1 hour
2. 2
   Otroresulting in a dark brown solution
3. 3
   TemperaturaUpon cooling
4. 4
   Otroprecipitation
5. 5
   OtroThe resulting precipitate was removed by filtration
6. 6
   Lavadowashed with water
7. 7
   OtroThe crude product was purified by flash chromatography
8. 8
   Lavadoeluting with 5% methanol/methylene chloride

Procedimiento

To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 2-naphthyl-acetonitrile (227 mg, 1.36 mmol). After stirring for 5 minutes at room temperature, 4-ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde (300 mg, 1.24 mmol) was added and the reaction heated at 110° C. for 1 hour, resulting in a dark brown solution. Upon cooling, the solution was poured into 30 mL of water which caused precipitation. The resulting precipitate was removed by filtration and washed with water. The crude product was purified by flash chromatography, eluting with 5% methanol/methylene chloride, followed by 10% methanol/methylene chloride. Concentration of product fractions yielded 400 mg (82%) of yellow solid, (8-ethyl-7-imino-6-naphthalen-2-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine; mp 236°-242° C.

Fuente