Reaktion #606992

Reaktionsgleichung

Ethyl acetate

ammonium chloride

2-[(trans-4-{6-[(2′-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propylpyrazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexyl)oxy]-N-methoxy-N-methylacetamide

methylmagnesium bromide

→

title compound

Ausbeute 95.0%

4′-({4-[trans-4-(2-hydroxypropoxy)cyclohexyl]-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile

Ausbeute 95.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with ethyl acetate
2. 2
   Waschenthe organic layer was washed with saturated brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethanol (6 mL)
6. 6
   workup.ADDITIONsodium borohydride (0.044 g) was added at 0° C
7. 7
   workup.STIRRINGAfter stirring at 0° C. for 1 hr
8. 8
   workup.ADDITIONethyl acetate and then saturated aqueous ammonium chloride solution were added
9. 9
   ExtraktionThe mixture was extracted with ethyl acetate
10. 10
    Waschenthe organic layer was washed with saturated brine
11. 11
    Trocknendried over anhydrous magnesium sulfate
12. 12
    Einengenconcentrated
13. 13
    SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

To a solution of 2-[(trans-4-{6-[(2′-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propylpyrazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexyl)oxy]-N-methoxy-N-methylacetamide (0.65 g) in tetrahydrofuran (6 mL) was added dropwise methylmagnesium bromide (1 M tetrahydrofuran solution, 2.3 mL) at 0° C., and the mixture was stirred for 1 hr. Ethyl acetate and then saturated aqueous ammonium chloride solution were added. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was dissolved in ethanol (6 mL), and sodium borohydride (0.044 g) was added at 0° C. After stirring at 0° C. for 1 hr, ethyl acetate and then saturated aqueous ammonium chloride solution were added. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.57 g, 95%).

Quelle