Boron tribromide → HCID 178432916, compound

Participants

Reaction Steps

To 2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)aniline (0.152 mmol, 66 mg) in dichloromethane (1.4 ml) at 0-5° C. was added boron tribromide (0.758 mmol, 73 μl) under a nitrogen atmosphere. Then the reaction mixture was stirred for three hours at room temperature. Then additional boron tribromide (0.758 mmol, 73 μl) was added. After 30 minutes the reaction mixture was quenched with methanol and stirred during the night. The solid formed was removed by filtration and the filtrate was concentrated in vacuo. Water was added and the mixture was coevaporated with toluene twice. The crude product was dissolved in methanol; sillica gel added, concentrated in vacuo and the residue charged on a silica gel column for purification (gradient of dichloromethane to dichloromethane/methanol 5/1) to give impure 2-amino-5-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenol (116 mg content approximately 20%) which was used without further purification.

Provenance & Evidence