Реакция #3316

Уравнение реакции

4-ethylamino-2-methylthio-5-pyrimidinecarboxylate ethyl ester

lithium aluminum hydride

→

4-ethylamino-2-methylthio-5-pyrimidinemethanol

Выход 92.0%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеthe reaction was carefully quenched with 4.5 mL of water, 4.5 mL of 15% NaOH, and 16 mL of water
2. 2
   ДругоеThe white precipitate was removed by filtration
3. 3
   Промывкаwashing with ethyl acetate
4. 4
   КонцентрированиеThe filtrate was concentrated in vacuo and 1:1 hexane
5. 5
   workup.ADDITIONethyl acetate was added
6. 6
   ДругоеThe solids were collected

Методика

A solution of 4-ethylamino-2-methylthio-5-pyrimidinecarboxylate ethyl ester (8.93 g, 37.1 mmol) in 100 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (2.30 g, 60.5 mmol) in 100 mL of tetrahydrofuran. After 10 minutes, the reaction was carefully quenched with 4.5 mL of water, 4.5 mL of 15% NaOH, and 16 mL of water, and the mixture was stirred for 1.5 hours. The white precipitate was removed by filtration washing with ethyl acetate. The filtrate was concentrated in vacuo and 1:1 hexane:ethyl acetate was added. The solids were collected to give 6.77 g (92%) of 4-ethylamino-2-methylthio-5-pyrimidinemethanol; mp 152°-156° C.

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