(S)-1-(1-Phenyl-1H-benzo[D]imidazol-2-YL)ethanamine → (S)-N4-(1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethyl)pyrimidine-4,6-diamine

Participants

Reaction Steps

A solution of (S)-1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethanamine from Example 4 (321.6 mg, 1.36 mmol, 1.00 equiv) in dioxane (10 mL) and 6-chloropyrimidin-4-amine hydrochloride (456.3 mg, 2.71 mmol, 2.00 equiv, 98%) was stirred overnight at 130° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a C18 column with acetonitrile/water (0-40%) to afford 298.6 mg (60%) of 146 hydrochloride as yellow crystals. LC-MS (ES, m/z): 331 [M+H]+H-NMR: (400 MHz, CD3OD, ppm) δ: 8.15 (s, 1H), 7.87-7.58 (m, 8H), 7.38-7.36 (m, 1H), 5.88 (br s, 1H), 5.41-5.36 (q, 1H), 1.747-1.73 (d, 3H)

Provenance & Evidence