반응 #3320

반응 방정식

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

수율 78.9%

용매

2-ethoxyethanol

반응 조건

후처리

1. 1
   온도the reaction heated at 120° C. for 2 hours
2. 2
   기타resulting in a dark brown solution
3. 3
   온도Upon cooling
4. 4
   기타precipitation
5. 5
   기타The resulting precipitate was removed by filtration
6. 6
   세척washed with water
7. 7
   기타The crude product was purified by flash chromatography
8. 8
   세척eluting with 5% methanol/methylene chloride

실험 절차

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.

출처