تفاعل #3320

معادلة التفاعل

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

المردود 78.9%

المذيبات

2-ethoxyethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction heated at 120° C. for 2 hours
2. 2
   أخرىresulting in a dark brown solution
3. 3
   درجة الحرارةUpon cooling
4. 4
   أخرىprecipitation
5. 5
   أخرىThe resulting precipitate was removed by filtration
6. 6
   غسيلwashed with water
7. 7
   أخرىThe crude product was purified by flash chromatography
8. 8
   غسيلeluting with 5% methanol/methylene chloride

الإجراء التجريبي

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.

المصدر