Reaktion #86542

Reaktionsgleichung

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

trimethylphosphine

EtOAc

→

desired product

Ausbeute 97.0%

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

Ausbeute 97.0%

Lösungsmittel

tetrahydrofuran

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To a stirred solutions of 7-(1-azidoethyl)-6-(3,5-difluorophenyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.15 g, 0.43 mmol) (1 st peak from chiral separation) in tetrahydrofuran (2 mL) and water (0.5 mL) were added 1.00 M of trimethylphosphine in tetrahydrofuran (0.52 mL, 0.52 mmol) at room temperature and the mixtures were stirred at room temperature for 1 hour. To the mixture was added EtOAc and the mixture was extracted with aqueous 1 N HCl solution (three times). The combined extracts were neutralized with solid Na2CO3 and extracted with dichloromethane (two times). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the desired product (134 mg, 96.6%). LCMS calculated for C15H14F2N3OS (M+H)+: m/z=322.1. Found: 322.0.

Quelle