Reaktion #3320

Reaktionsgleichung

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

Ausbeute 78.9%

Lösungsmittel

2-ethoxyethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction heated at 120° C. for 2 hours
2. 2
   Sonstigeresulting in a dark brown solution
3. 3
   TemperaturUpon cooling
4. 4
   Sonstigeprecipitation
5. 5
   SonstigeThe resulting precipitate was removed by filtration
6. 6
   Waschenwashed with water
7. 7
   SonstigeThe crude product was purified by flash chromatography
8. 8
   Wascheneluting with 5% methanol/methylene chloride

Vorschrift

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.

Quelle