4-Amino-6-methoxypyrimidine → 1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(6-methoxypyrimidin-4-yl)isoquinoline-6-sulfonamide

Participants

Reaction Steps

To a vial containing 6-methoxypyrimidin-4-amine (0.063, 0.503 mmol) in 2Me-THF (1 ml) was added lithium bis(trimethylsilyl)amide (237 μl, 0.237 mmol) at −78° C. and stirred for 1 h. To this was then added a solution of perfluorophenyl 1-(2-methoxy-4-(trifluoromethyl)phenyl)isoquinoline-6-sulfonate (Intermediate LLL; 100 mg, 0.182 mmol) in 2Me-THF (1 ml) at −78° C. dropwise and stirred for 1 h. Reaction mixture was quenched with 3 drops of methanol and purified via reverse-phase chromatography with 0.1% NH4OH in ACN and water as mobile phase to obtain 1-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(6-methoxypyrimidin-4-yl)isoquinoline-6-sulfonamide (0.005 g, 6%) as white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.77 (d, J=5.77 Hz, 1H) 8.63 (s, 1H) 8.52-8.56 (m, 1H) 7.82-7.89 (m, 2H) 7.77 (d, J=8.80 Hz, 1H) 7.50 (d, J=7.83 Hz, 1H) 7.41 (d, J=8.12 Hz, 1H) 7.28 (br. s., 2H) 3.96 (s, 3H) 3.75 (s, 3H); m/z (ESI) 491.1 (M+H)+.

Provenance & Evidence