Reaktion #86552

Reaktionsgleichung

7-(1-azidoethyl)-6-(3-fluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

trimethylphosphine

ethyl acetate

→

desired product

Ausbeute 58.8%

7-(1-aminoethyl)-6-(3-fluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Ausbeute 58.8%

Lösungsmittel

tetrahydrofuran

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with aqueous 1 N HCl solution (three times)
2. 2
   ExtraktionThe combined extract
3. 3
   Extraktionextracted with dichloromethane (two times)
4. 4
   WaschenThe combined organic layer was washed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated

Vorschrift

To a stirred solution of 7-(1-azidoethyl)-6-(3-fluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.32 g, 1.0 mmol) in tetrahydrofuran (5 mL) and water (1 mL) was added 1.00 M of trimethylphosphine in tetrahydrofuran (1.22 mL, 1.22 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. To the mixture was added ethyl acetate, and the mixture was extracted with aqueous 1 N HCl solution (three times). The combined extract was neutralized with solid NaHCO3 and extracted with dichloromethane (two times). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated to give the desired product (0.17 g, 58%). LCMS calculated for C14H13FN3OS (M+H)+: m/z=290.1. Found: 290.0.

Quelle