Reaktion #169154

Reaktionsgleichung

Sodium hexamethyldisilazide

2,6-diethylaniline

ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

→

title compound

Ausbeute 80.0%

8-Amino-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Ausbeute 80.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature over a period of 30 min
2. 2
   workup.STIRRINGAfter stirring at room temperature for 3 h
3. 3
   Sonstigethe reaction was quenched by the addiction of saturated acquesous NH4Cl (10 mL)
4. 4
   SonstigeThe reaction was partitioned between ethyl acetate (50 mL) and water (50 mL)
5. 5
   ExtraktionThe acqueos layer was extracted with ethyl acetate (2×30 mL)
6. 6
   WaschenThe combined organic solution was washed with brine (50 mL)
7. 7
   Trocknendried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated to dryness
10. 10
    Sonstigethe crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 95/5)

Vorschrift

Sodium hexamethyldisilazide (NaHMDS) in THF (1.0 M, 11.0 mL, 11.0 mmol) was added over 30 min to a solution of 2,6-diethylaniline (1.2 mL, 8.32 mmol) and ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (0.760 g, 2.77 mmol) in THF (30 mL) at 0° C. The resulting brown solution was stirred at 0° C. for 10 min and allowed to warm to room temperature over a period of 30 min. After stirring at room temperature for 3 h, the reaction was quenched by the addiction of saturated acquesous NH4Cl (10 mL). The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL). The acqueos layer was extracted with ethyl acetate (2×30 mL). The combined organic solution was washed with brine (50 mL), dried over Na2SO4, filtered and evaporated to dryness, the crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 95/5) to afford 0.830 g (80% yield) of the title compound.

Quelle