4-Aminopyridine → HCID 68032340, compound

Participants

Reaction Steps

This compound was synthesized in an analogous manner to 21 utilizing benzyl 2,2,2-trifluoroacetate in step 1. To a solution of 4-aminopyridine (17.38 mg, 0.185 mmol) in THF (92 μl) cooled to −78° C. under nitrogen, LiHMDS (852 μl, 0.852 mmol) was added dropwise. The reaction mixture was warmed up to rt, then was stirred for 30 minutes. To the reaction mixture cooled back to −78° C., 2-(methylsulfinyl)-4′-(trifluoromethyl)-4,5′-bipyrimidin-2′-amine (14 mg, 0.046 mmol) was added, and the reaction mixture was warmed up to rt, then was stirred for 1 hour. The crude product was purified by reverse-phase HPLC [30-100% organic phase over 15 minutes] followed by Biotage™ silica gel chromatography [10 g SNAP column, 100% DCM to 12% MeOH/DCM] to obtain the desired product as a pale yellow solid (3.98 mg, 25% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.13 (d, J=4.52 Hz, 1H) 7.67 (br. s., 2H) 7.77 (d, J=6.02 Hz, 2H) 8.34 (d, J=6.02 Hz, 2H) 8.56-8.74 (m, 2H) 10.23 (s, 1H). HRMS (ES+) for C14H10F3N7.H+ [MH+]: calcd, 334.1028; found, 334.1037. UV-LC: 97.31/100% UV purity at 214/254 nm; tR=2.47 minutes over 7.75 minutes.

Provenance & Evidence