Reaktion #3265

Reaktionsgleichung

4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester

lithium aluminum hydride

→

4-methylamino-2-methylsulfanyl-5-pyrimidinemethanol

Ausbeute 84.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 10 minutes the reaction was carefully quenched with 2 mL of water, 2 mL of 15% NaOH
2. 2
   Sonstigethe white precipitate which had formed
3. 3
   Sonstigewas removed by filtration
4. 4
   Waschenwas washed with ethyl acetate
5. 5
   EinengenThe filtrate was concentrated in vacuo and 3:1 hexane
6. 6
   workup.ADDITIONethyl acetate was added
7. 7
   SonstigeThe solids were collected

Vorschrift

A solution of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (4.36 g, 19.3 mmol) in 60 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (1.10 g, 29.0 mmol) in 40 mL of tetrahydrofuran. After 10 minutes the reaction was carefully quenched with 2 mL of water, 2 mL of 15% NaOH, and an additional 7 mL of water. The mixture was stirred for 1 hour, and the white precipitate which had formed was removed by filtration, and was washed with ethyl acetate. The filtrate was concentrated in vacuo and 3:1 hexane:ethyl acetate was added. The solids were collected to give 2.99 g (84%) of 4-methylamino-2-methylsulfanyl-5-pyrimidinemethanol; mp 155°-157° C.

Quelle