2-Amino-4-chloropyrimidine → (S)-N4-(1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethyl)pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

Into a 25-mL round-bottom flask was placed a solution of (S)-1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethanamine from Example 4 (238 mg, 1.00 mmol, 1.00 equiv) in ethanol (8 mL) and 4-chloropyrimidin-2-amine (130 mg, 0.99 mmol, 0.98 equiv, 98%). The resulting solution was stirred overnight at 100° C. and concentrated under vacuum. The crude product was applied onto a C18 Column (water/acetonitrile) to afford 150 mg (44%) of 145 as a white solid. LC-MS (ES, m/z): 331 [M+H]+ H-NMR (300 MHz, CD3OD, ppm): δ 7.83 (d, 1H), 7.57 (m, 8H), 6.11 (q, 1H), 5.61 (q, 1H), 1.67 (d, 3H)

Provenance & Evidence