Cyclohexylamine → N2-Cyclohexyl-4'-cyclopropylmethyl-N2'-methyl-[4,5']bipyrimidinyl-2,2'-diamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4′-(cyclopropylmethyl)-N-methyl-2-(methylsulfinyl)-4,5′-bipyrimidin-2′-amine (5-1) (50 mg, 0.165 mmol) in DMSO (1 mL), cyclohexylamine (94 μL, 0.824 mmol) was added, and the reaction was heated in the microwave at 160° C. for 10 minutes. The crude reaction was purified by reverse-phase HPLC [30-100% organic phase with 3% n-propanol modifier over 15 minutes] followed by Biotage™ silica gel chromatography [10 g SNAP column, 100% DCM to 10% MeOH/DCM] to obtain the pure desired product as a white solid (39.0 mg, 69.9% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.04-0.20 (m, 2H) 0.37 (d, J=7.58 Hz, 2 H) 0.99-1.19 (m, 2 H) 1.19-1.36 (m, 4 H) 1.59 (d, J=11.62 Hz, 1 H) 1.65-1.80 (m, 2 H) 1.88 (d, J=8.59 Hz, 2 H) 2.72-2.90 (m, 5 H) 3.63-3.80 (m, 1 H) 6.68 (d, J=5.05 Hz, 1 H) 6.96 (d, J=8.08 Hz, 1 H) 7.29 (br. s., 1 H) 8.24 (d, J=5.05 Hz, 1 H) 8.36 (br. s., 1 H). HRMS (ES+) for C19 H26N6.H+ [MH+]: calcd, 339.2297. found, 339.2312. UV-LC: 100% UV purity at 254/214 nm; tR=6.70 minutes over 7.75 minutes.

Provenance & Evidence