Triethylamine → 6-Chloro-2,4,8,19,23-pentazatetracyclo[15.3.1.13,7.110,14]tricosa-1(20),3,5,7(23),10(22),11,13,17(21),18-nonaen-13-amine

Participants

Reaction Steps

Into a reaction flask were added N-{4-amino-3-[2-(5-aminopyridin-3-yl)ethyl]benzyl}-2,5-dichloropyrimidin-4-amine trihydrochloride (0.29 g, 0.74 mmol), 1,4-dioxane (5 mL), and triethylamine (0.31 mL, 2.2 mmol). The mixture was stirred at rt under N2 for 5 minutes, followed by an addition of palladium acetate (5 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (12.9 mg, 0.02 mmol), and cesium carbonate (500 mg, 2.0 mmol). The reaction mixture was degassed with N2 bubbling. The tube was then sealed and heated at 160° C. for 2 hours. After concentration, the crude product was purified by silica gel column chromatography to give the desired product as a white powder (100 mg, 42%). LCMS for C18H18ClN6 (M+H)+: m/z=353.0. 1H NMR (400 MHz, DMSO-d6): δ 9.65 (s, 1H), 8.44 (d, J=1.6 Hz, 2H), 8.16 (d, J=2.3 Hz, 1H), 8.01 (s, 1H), 7.11 (m, 2H), 7.03 (m, 2H), 6.69 (s, 1H), 4.14 (d, J=5.8 Hz, 2H), 2.88 (m, 4H).

Provenance & Evidence