Diisopropylethylamine → N4-(1-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-3-yl)-N4-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(3,4-dichlorobenzyl)-N-methyl-1,2,3,4-tetrahydroquinolin-3-amine TFA salt (200 mg, 0.52 mmol) and 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine (211 mg, 1.24 mmol) in dimethylacetamide (5 mL) was treated with diisopropylethylamine (0.327 ml, 3.5 eq). The mixture was heated at 120° C. for 22 hours. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was separated, washed with water and dried. The residue was purified by flash column (eluted with ethyl acetate:hexane: 1:1 to 100% ethyl acetate) to give N4-(1-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-3-yl)-N4-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine as a cream solid (140 mg). 1H NMR (DMSO) 400 MHz δ 12.52 (s, 1H), 7.84 (br, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.52 (d, J=2.0 Hz, 1H), 7.27 (dd, J=2.0 Hz and 8.4 Hz, 1H), 7.13 (brs, 1H), 6.98 (d, J=6.8 Hz, 1H), 6.94 (t, J=7.2 Hz, 1H), 6.55 (t, J=7.2 Hz, 1H), 6.49 (d, J=8.4 Hz, 1H), 6.0 (brs, 2H), 5.48 (br, 1H), 4.51 (dd, J=17.2 Hz and 58.0 Hz, 2H), 3.59 (t, J=10.4 Hz, 1H), 3.30 (m, 1H), 3.18 (s, 3H), 2.79 (m, 1H). LCMS m/e 455 (M+H).

Provenance & Evidence