Reaktion #41040

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 48.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe product extracted with ethyl acetate
2. 2
   WaschenThe organic phase washed with brine
3. 3
   Trocknendried (Na2SO4)
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (95-5-0.5)

Vorschrift

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.

Quelle