Reacción #41040

Ecuación de reacción

4-[5-(3-methyl-thiophen-2-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-butyraldehyde

(1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane

AcOH

NaBH(AcO)3

dichloroethane

NaOH

→

title compound

Rendimiento 48.0%

5-(3-methyl-2-thienyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione hydrochloride

Rendimiento 48.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe product extracted with ethyl acetate
2. 2
   LavadoThe organic phase washed with brine
3. 3
   Secadodried (Na2SO4)
4. 4
   Otroevaporated
5. 5
   OtroThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (95-5-0.5)

Procedimiento

To a solution of 4-[5-(3-methyl-thiophen-2-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-butyraldehyde (Prep32, 30 mg, 0.11 mmol), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 21 mg, 0.09 mmol), AcOH (6 μl, 0.1 mmol) in dichloroethane (1.5 mL) and NaBH(AcO)3 (24 mg, 0.11 mmol) were added at 0° C. The reaction was stirred for 30 minutes at room temperature then 2N NaOH (1 mL) was added and the product extracted with ethyl acetate. The organic phase washed with brine, dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (95-5-0.5) to give the title compound (26 mg, 48% yield) as a free base.

Fuente