Benzophenone imine → 5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (3.25 g, 10 mmol) sodium t-butoxide (0.600 g, 6.25 mmol), and BINAP (0.170 g, 0.27 mmol) in 120 mL of toluene was purged with nitrogen for ca. 20 min. Pd2(dba)3 (0.080 g, 0.077 mmol) and benzophenone imine (2.16 mL, 12.9 mmol) were added, and the mixture was stirred at 130° C. for 12 h. The mixture was filtered through Celite and concentrated. The resulting residue was dissolved in 50 mL of methanol. Sodium acetate (4.93 g, 36 mmol) and hydroxylamine hydrochloride (2.09 g, 30 mmol) were added, and the mixture was stirred for 45 min. then concentrated. The resulting residue was partitioned between a 0.1 M NaOH solution and dichloromethane, and the organic layer was dried over Na2SO4, filtered and concentrated to a residue. Column chromatography afforded 3.0 g (75%) of 5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine.

Provenance & Evidence