Water → HCID 59400113, compound

Participants

Reaction Steps

1-(2,4-difluorobenzyl)-1,2,3,4-tetrahydroquinolin-3-amine, 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine (200 mg, 1.2 mmol) and diisopropylethylamine (1 mL) in dimethylacetamide (6 mL) was stirred at 126° C. for 20 hours. After cooling to room temperature, water (15 mL) was added and the mixture extracted with ethyl acetate (3×15 mL). The combined organics were dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (100% ethyl acetate) to provide N4-(1-(2,4-difluorobenzyl)-1,2,3,4-tetrahydroquinolin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine as a light yellow solid (160 mg). M.p.=110-114° C. 1H NMR (DMSO-d6, 400 MHz) δ 12.43 (s, 1H), 7.83 (s, 1H), 7.62 (d, J=6.0 Hz, 1H), 7.34-7.21 (m, 2H), 7.03-6.95 (m, 3H), 6.58-6.54 (m, 2H), 6.00 (s, 2H), 4.66 (br, 1H), 4.54 (m, 2H), 3.55-3.51 (m, 1H), 3.39-3.29 (m, 1H), 3.09-3.04 (m, 1H), 2.89-2.81 (m, 1H). LCMS m/e 408 (M+1).

Provenance & Evidence