Diisopropylethylamine → 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methyl-2-pyridin-2-yl-ethyl)-amide

Participants

Reaction Steps

2-Bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (300 mg, 0.81 mmol), 1-(pyridin-2-yl)propan-2-amine (165 mg, 1.21 mmol) and DIPEA (312 mg, 2.42 mmol) were combined with DMF (5 mL) to give a yellow solution. HATU (306 mg, 0.81 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with brine and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water and brine then dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-5% methanol in dichloromethane) to afford 360 mg (86%) of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methyl-2-pyridin-2-yl-ethyl)-amide as a yellow oil. MS: (M+H)+=491.

Provenance & Evidence