Triethylamine → 6-Fluoro-2,4,8,17,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaene

Participants

Reaction Steps

To a mixture of N-{3-[2-(4-aminopyridin-2-yl)ethyl]phenyl}-2-chloro-5-fluoropyrimidin-4-amine dihydrochloride (50.0 mg, 0.12 mmol) and triethylamine (0.05 mL, 0.36 mmol) in dry 1,4-dioxane (1.0 mL) was added (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4.16 mg, 0.007 mmol), palladium acetate (1.1 mg, 0.0048 mmol) and cesium carbonate (78.2 mg, 0.24 mmol). The cloudy mixture was degassed by bubbling N2 through the solution. The sealed tube was then microwaved at 150° C. for 30 min. The reaction mixture was diluted with THF, filtered and concentrated to give the residue, which was then triturated with MeOH/THF/EtOAc to provide the desired product as a white powder (15 mg, 41%). LCMS for C17H15FN5 (M+H)+: m/z=308.0. 1H NMR (400 MHz, DMSO-d6): δ 9.68 (s, 1H), 9.58 (s, 1H), 8.14 (m, 3H), 7.84 (s, 1H), 7.26 (dd, J=15.2, 7.2 Hz, 1H), 7.04 (dd, J=7.2, 2.0 Hz, 2H), 6.84 (dd, J=5.6, 2.0 Hz, 1H), 2.90 (m, 4H).

Provenance & Evidence