Triethylamine → 6-Chloro-2,4,8,19,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaene

To a mixture of N-{3-[2-(2-aminopyridin-4-yl)ethyl]phenyl}-2,5-dichloropyrimidin-4-amine dihydrochloride (35.0 mg, 0.08 mmol) and triethylamine (0.034 mL, 0.24 mmol) in a mixed solvent of 1,4-dioxane (0.70 mL) and N,N-dimethylformamide (0.70 mL) at rt were added (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.6 mg, 0.010 mmol), palladium acetate (2.2 mg, 0.010 mmol) and cesium carbonate (52.6 mg, 0.16 mmol). The mixture was degassed by bubbling N2 through the solution. The sealed tube was then microwaved at 160° C. for 20 min. The reaction mixture was diluted with THF/MeOH, filtered and concentrated to give a residue, which was triturated with MeOH/EtOAc (1:1) to provide the desired product (16 mg, 61%) as a light brown powder. LCMS for C17H15ClN5 (M+H)+: m/z=324.0. 1H NMR (400 MHz, DMSO-d6): δ 9.44 (s, 1H), 9.22 (s, 1H), 8.18 (m, 1H), 8.06 (m, 1H), 7.86 (m, 1H), 7.68 (m, 1H), 7.40 (m, 1H), 7.28 (m, 1H), 7.05 (m, 1H), 6.28 (m, 1H), 3.05 (m, 4H).

1. customThe mixture was degassed
2. customby bubbling N2 through the solution
3. customThe sealed tube was then microwaved at 160° C. for 20 min
4. additionThe reaction mixture was diluted with THF/MeOH
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a residue, which
8. customwas triturated with MeOH/EtOAc (1:1)

ORD record

ord-c8d2eb2096484338a992638861efc974

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871753B2