反応 #41040

反応方程式

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

収率 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

収率 48.0%

反応条件

後処理

1. 1
   抽出the product extracted with ethyl acetate
2. 2
   洗浄The organic phase washed with brine
3. 3
   乾燥dried (Na2SO4)
4. 4
   その他evaporated
5. 5
   その他The crude was purified by flash chromatography with DCM-MeOH—NH4OH (95-5-0.5)

実験手順

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.

出典