Reaktion #3316

Reaktionsgleichung

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

lithium aluminum hydride

→

4-ethylamino-2-methylthio-5-pyrimidinemethanol

Ausbeute 92.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle