Tin atom → ((S)-1-methanesulfonyl-piperidin-3-yl)-{2-methylsulfanyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine

Participants

Reaction Conditions

Reaction Steps

A degassed toluene solution of 2-bromo-5-(2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (200 mg, 0.61 mmol) and 1,1,1,2,2,2-hexamethyldistannane (220 mg, 0.67 mmol) was treated with tetrakistriphenylphosphine palladium (0) (35 mg, 0.03 mmol) and heated to 95-100° C. for 2 hours. When LCMS indicated conversion to the tin product, 5-(2-trimethylsilanyl-ethoxymethyl)-2-trimethylstannanyl-5H-pyrrolo[2,3-b]pyrazine, (MS (ES+): 412), the reaction was treated with (5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-((S)-1-methanesulfonyl-piperidin-3-yl)-amine (80 mg, 0.21 mmol) and additional tetrakistriphenylphosphine palladium (0) (35 mg, 0.03 mmol) and heated to 100° C. for 16 hours. The reaction was cooled, filtered through celite, evaporated and purified by flash chromatography (60% ethyl acetate/hexane+2% triethylamine) to give 60 mg of ((S)-1-methanesulfonyl-piperidin-3-yl)-{2-methylsulfanyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine. MS (ES+): 550.

Provenance & Evidence