Diisopropylethylamine → HCID 59400116, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-phenyl-1,2,3,4-tetrahydroquinolin-3-amine TFA salt (325 mg, 0.96 mmol) and 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine (325 mg, 1.92 mmol) in dimethylacetamide (4 mL) was treated with diisopropylethylamine (0.5 ml, 3 eq). The mixture was heated at 120° C. for 20 hours. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate. The organic layer was further washed with brine and dried over anhydrous sodium sulfate. The residue was purified by flash column (eluted with ethyl acetate:hexane: 40% to 100% ethyl acetate) to give N4-(1-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine as a yellow a solid (240 mg). M.p.=88-92° C. 1H NMR (DMSO) 400 MHz δ 12.39 (s, 1H), 7.80 (s, br, 1H), 7.64 (d, J=6.8 Hz, 1H), 7.35-7.25 (m, 2H), 7.23 (m, 2H), 7.07 (m, 2H), 6.92 (m, 1H), 6.69 (m, 2H), 5.96 (s, 1H), 4.66 (s, br, 1H), 3.85 (m, 1H), 3.47 (m, 1H), 3.14 (dd, J=5.6 and 10.0 Hz, 1H), 2.88 (m, 1H). LCMS m/e 348 (M+H).

Provenance & Evidence