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

Temperatur

140 °C

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).

1. customThis was then purged with argon
2. additionTo this mixture was then added
3. customdegassed toluene (8 mL)
4. customThe mixture was then purged with argon again
5. customa further 4 h
6. customat 135° C
7. temperatureThe mixture was cooled
8. additiondiluted with ethyl acetate
9. washwashing with more ethyl acetate
10. concentrationThe dark solution was concentrated in vacuo
11. customThe residue was purified by FCC

ORD-Eintrag

ord-edfc02741a3e4efc8d0edf36bb885728

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09440974B2