4-Aminopyridine → HCID 67983712, compound

Participants

Reaction Steps

To a solution of 4-aminopyridine (423 mg, 4.49 mmol) in THF (0.562 mL) cooled to −10° C. was added LHMDS (1M in THF) (1.123 mL, 1.123 mmol). The resulting suspension was warmed to rt and stirred for 15 minutes, after which time it was cooled back to −10° C. and 2-Methanesulfinyl-4′-methyl-[4,5′]bipyrimidinyl-2′-ylamine (20) (70 mg, 0.281 mmol) was then added. The reaction mixture was again warmed to rt and stirred for 1.5 hours. The reaction was quenched by slow addition of saturated ammonium chloride and the volatiles evaporated. The mixture was then diluted with DCM, the layers separated, and the organic layer washed with brine, dried with sodium sulfate, and concentrated. The crude residue was purified by flash column chromatography with a gradient of 2-20% MeOH in DCM. The product was further purified by reverse phase HPLC with a gradient of 10-90% MeCN in water over 15 minutes, to give the desired product as a white solid (1.39 mg, 0.44%). 1H NMR (400 MHz, MeOD) δ ppm 2.57 (s, 3 H) 7.13 (d, J=5.56 Hz, 1 H) 7.84 (d, J=6.57 Hz, 2 H) 8.30 (d, J=6.57 Hz, 2 H) 8.50 (s, 1 H) 8.57 (d, J=5.05 Hz, 1 H). HRMS (ES+) for C14 H13N7.H+ [MH+]: calcd, 280.1311. found, 280.1318. UV-LC: 100/100% UV purity at 214/254 nm; tR=2.93 minutes over 7.75 minutes.

Provenance & Evidence