반응 #3318

반응 방정식

4-ethylamino-2-phenylamino-pyrimidine-5-carboxylic acid ethyl ester

lithium aluminum hydride

lithium aluminum hydride

→

(4-ethylamino-2-phenylamino-pyrimidin-5-yl)methanol

수율 39.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.WAITwas continued for 30 minutes
2. 2
   기타The reaction was carefully quenched with 120 μL of water, 200 μL of 15% NaOH, and 300 μL of water
3. 3
   workup.STIRRINGAfter stirring for 1 hour
4. 4
   기타the white precipitate was removed by filtration
5. 5
   세척washing with ethyl acetate
6. 6
   농축The filtrate was concentrated in vacuo
7. 7
   기타the crude material was purified by flash chromatography
8. 8
   세척eluting with ethyl acetate

실험 절차

A solution of 4-ethylamino-2-phenylamino-pyrimidine-5-carboxylic acid ethyl ester (109 mg, 0.38 mmol) in 6 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (35 mg, 0.92 mmol) in 5 mL of tetrahydrofuran. After 25 minutes, an additional 30 mg of lithium aluminum hydride was added, and stirring was continued for 30 minutes. The reaction was carefully quenched with 120 μL of water, 200 μL of 15% NaOH, and 300 μL of water. After stirring for 1 hour, the white precipitate was removed by filtration washing with ethyl acetate. The filtrate was concentrated in vacuo, and the crude material was purified by flash chromatography eluting with ethyl acetate to provide 36 mg (39%) of (4-ethylamino-2-phenylamino-pyrimidin-5-yl)methanol; mp 174°-176° C.

출처