Reaktion #41081

Reaktionsgleichung

3-[5-(2-chloro-pyridin-3-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-propionaldehyde

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

NaBH(AcO)3

NaOH

→

title compound

Ausbeute 34.0%

5-(2-chloro-3-pyridinyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione dihydrochloride

Ausbeute 34.0%

Lösungsmittel

dichloroethane MeOH

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe product was extracted with DCM
2. 2
   TrocknenThe organic phase was dried (Na2SO4)
3. 3
   Sonstigeevaporated
4. 4
   SonstigeThe crude was purified by flash chromatography
5. 5
   Wascheneluting with DCM-MeOH—NH4OH (98:2:0.2)

Vorschrift

A solution of 3-[5-(2-chloro-pyridin-3-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-propionaldehyde (Prep97, 128 mg, 0.46 mmol), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 104 mg, 0.46 mmol), and AcOH (32 μl) in dichloroethane-MeOH (10-01, 4 ml) was cooled to 0° C. NaBH(AcO)3 (102 mg, 0.48 mmol) was added portionwise. The mixture was stirred at 0° C. for further 1 hour and then basified with 1N NaOH. The product was extracted with DCM. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography eluting with DCM-MeOH—NH4OH (98:2:0.2) to give 77 mg of the free base of title compound (34% yield).

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