Reacción #3320

Ecuación de reacción

water

3-thiopheneacetonitrile

NaH

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

→

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

Rendimiento 78.9%

Disolventes

2-ethoxyethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction heated at 120° C. for 2 hours
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 3-thiopheneacetonitrile (168 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 120° C. for 2 hours, resulting in a dark brown solution. Upon cooling, the solution was poured into 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 340 mg (78%) of (8-ethyl-7-imino-6-thiophen-3-yl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine; mp 220°-222° C.

Fuente