Реакция #3320

Уравнение реакции

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

Выход 78.9%

Растворители

2-ethoxyethanol

Условия реакции

Обработка

1. 1
   Температураthe reaction heated at 120° C. for 2 hours
2. 2
   Другоеresulting in a dark brown solution
3. 3
   ТемператураUpon cooling
4. 4
   Другоеprecipitation
5. 5
   ДругоеThe resulting precipitate was removed by filtration
6. 6
   Промывкаwashed with water
7. 7
   ДругоеThe crude product was purified by flash chromatography
8. 8
   Промывкаeluting with 5% methanol/methylene chloride

Методика

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.

Источник