Reaktion #88922

Reaktionsgleichung

trans-N,N-dimethylcyclohexane-1,2-diamine

5-tert-Butyl-2H-pyrazol-3-ylamine

potassium carbonate

3-bromo-5-methylphenol

→

title compound

Ausbeute 49.2%

3-(5-Amino-3-tert-butyl-pyrazol-1-yl)-5-methyl-phenol

Ausbeute 49.2%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis was then purged with argon
2. 2
   workup.ADDITIONTo this mixture was then added
3. 3
   Sonstigedegassed toluene (8 mL)
4. 4
   SonstigeThe mixture was then purged with argon again
5. 5
   Sonstigea further 4 h
6. 6
   Sonstigeat 135° C
7. 7
   TemperaturThe mixture was cooled
8. 8
   workup.ADDITIONdiluted with ethyl acetate
9. 9
   Waschenwashing with more ethyl acetate
10. 10
    EinengenThe dark solution was concentrated in vacuo
11. 11
    SonstigeThe residue was purified by FCC

Vorschrift

5-tert-Butyl-2H-pyrazol-3-ylamine (1.11 g, 8.00 mmol), potassium carbonate (2.32 g, 16.8 mmol), copper (I) iodide (0.076 g, 0.40 mmol), and 3-bromo-5-methylphenol (1.80 g, 9.60 mmol) were weighed into a large microwave vial. This was then purged with argon then trans-N,N-dimethylcyclohexane-1,2-diamine (0.25 mL, 1.60 mmol) added. To this mixture was then added degassed toluene (8 mL). The mixture was then purged with argon again, the vial sealed, and heated for 1 h at 140° C. in the microwave, then a further 4 h at 135° C. The mixture was cooled, diluted with ethyl acetate and passed through a pad of celite/silica, washing with more ethyl acetate. The dark solution was concentrated in vacuo. The residue was purified by FCC, using 0-40% DCM in EtOAc, to give the title compound (966 mg, 49%). 1H NMR (300 MHz, CDCl3): 1.32 (9H, s), 2.24 (3H, s), 3.82 (2H, br s), 5.49 (1H, s), 6.45-6.52 (1H, m), 6.65-6.71 (1H, m), 6.85-6.91 (1H, m).

Quelle