Hydrochloric Acid → HCID 86687469, compound

Participants

Reaction Steps

To a flask containing ice cold suspension of pyrimidin-4-amine (0.402 g, 4.23 mmol) in THF (5.42 ml) was added lithium bis(trimethylsilyl)amide (1M in THF) (1.550 ml, 1.550 mmol) drop wise over 10 min. The mixture was stirred for 15 min providing a white suspension. A solution of perfluorophenyl 4-bromoisoquinoline-7-sulfonate (0.640 g, 1.409 mmol) in THF (5.0 ml) was added drop wise and the resulting mixture stirred for 1 hr. To the solution was added acetic acid (500 μl) and the solution dried under reduced pressure. The crude material was purified with a 40 g HP Silicycle column (SiliCycle, Inc. Quebec City, Canada) ramping EtOAc in heptane (0 to 25%) to elute starting material, then MeOH in DCM (0 to 20%) providing product which had coeluted with aminopyrimidine. The mixture was purified with a 10 g PE-AX column (Biotage AB, Uppsala, Sweden) washing with MeOH, then about 3% HCl in MeOH to provide 4-bromo-N-(pyrimidin-4-yl)isoquinoline-7-sulfonamide (Intermediate OOOO) (0.125 g, 0.342 mmol, 24.29% yield) as a white solid (possibly HCl salt). m/z (ESI) 365.1 (M+H)+.

Provenance & Evidence