Pyrazol-3-ylamine → 6-Chloro-1,4,7,9,9b-pentaaza-cyclopenta[a]naphthalene

Participants

Reaction Steps

The product from Example 1a (1.24 g, 7.01 mmol) in 30 mL of THF was reacted with 5-aminopyrazole (0.58 g, 7.01 mmol) in 10 mL of THF under an argon atmosphere by dropwise addition. The mixture was stirred at room temperature for 1 hour and then added diisopropylethylamine (1.22 mL, 7.01 mmol) dropwise with stirring. The mixture was heated overnight at 60° C., and quenched with water and extracted with EtOAc, washed with brine, and dried over Na2SO4. The product was filtered and the solvent was removed under vacuum. The product was purified by silica gel chromatography eluting with EtOAc/hexane to give the title compound as a pale yellow solid (405 mg, 29%).

Provenance & Evidence