1H-Pyrazol-3-amine, 5-methyl- → HCID 178428230, compound

Participants

Reaction Conditions

Reaction Steps

Degassed toluene (6 ml) and ethanol (3 ml) were added in one portion to a mixture of 4-bromo-2-phenyl-2H-phthalazin-1-one (0.750 g, 2.5 mmol), sodium t-butoxide (0.337 g, 3.5 mmol), 3-amino-5-methyl pyrazole (0.291 g, 3 mmol), tris-(dibenzylideneacetone)-dipalladium (0.115 g, 0.125 mmol) and 2-(di-t-butylphosphino)-biphenyl (0.075 g, 0.25 mmol) under nitrogen. The reaction mixture was heated to 100° C. for 20 hours with stirring and then cooled to room temperature. Diethyl ether (10 ml) was added and the precipitated solid was filtered to give the crude product as a grey solid (0.6 g, 76% yield). A 0.06 g portion of the crude product was triturated with acetonitrile (2 ml) and water (2 ml) to give the target compound (0.045 g, 58% yield based on recovered materials). 1H-NMR: (400 MHz, D6-DMSO) 11.96 (1H, s), 9.33 (1H, s), 8.53 (1H, d), 8.38 (1H, d), 7.92–7.99 (2H, m), 7.88 (2H, d), 7.77 (2H, t) 7.34 (1H, t) 6.24 (1H, s) 2.18 (3H, s) MS (ESI+)=(M+H)+ 318.29.

Provenance & Evidence