Reaktion #88932

Reaktionsgleichung

3-(Tert-butyl)-1H-pyrazol-5-amine

Intermediate 61b

(5-Iodo-2-triisopropylsilanyloxy-phenyl)-methanol

potassium carbonate

(1S,2S)—N,N′-bis-methyl-1,2-cyclohexane-diamine

→

title compound

Ausbeute 15.0%

[5-(5-Amino-3-tert-butyl-pyrazol-1-yl)-2-triisopropylsilanyloxy-phenyl]-methanol

Ausbeute 15.0%

Lösungsmittel

EtOAc

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed
2. 2
   Sonstigemicrowave irradiation
3. 3
   Temperaturthe reaction mixture heated at 150° C. for a further 1 h
4. 4
   Sonstigemicrowave irradiation
5. 5
   Sonstigethe phases separated
6. 6
   ExtraktionThe aqueous layer was then extracted with EtOAc (2×)
7. 7
   WaschenThe combined organic layers were washed with brine
8. 8
   Trocknendried (Na2SO4)
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated in vacuo
11. 11
    SonstigeThe organic layer was evaporated in vacuo
12. 12
    SonstigeThe residue was purified by FCC

Vorschrift

3-(Tert-butyl)-1H-pyrazol-5-amine (0.32 g, 2.30 mmol) was treated with a solution of Intermediate 61b (1.04 g, 2.60 mmol) in toluene (4 mL) then potassium carbonate (0.68 g, 4.90 mmol), (1S,2S)—N,N′-bis-methyl-1,2-cyclohexane-diamine (0.07 g, 0.47 mmol) and copper (I) iodide (0.022 g, 0.11 mmol) were added. The mixture was degassed then heated at 150° C. for 1 h using microwave irradiation. Another portion of copper (I) iodide (0.022 g, 0.11 mmol) was added and the reaction mixture heated at 150° C. for a further 1 h using microwave irradiation. The mixture was diluted with EtOAc and water and the phases separated. The aqueous layer was then extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The organic layer was evaporated in vacuo. The residue was purified by FCC, using 0-15% EtOAc in DCM, to give the title compound (0.14 g, 15%). LCMS (Method 3): Rt 3.87 min, m/z 418 [MH+].

Quelle