4-Methoxy-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amine → 1-(1-Ethyl-3-methyl-1H-pyrazol-4-yl)-8-(4-methoxy-2-methylamino-pyrimidin-5-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Participants

Reaction Steps

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate F) and [4-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-yl]-methyl-amine (stage 236.1.1) to give the title compound as a white solid. (HPLC: tR 2.19 min (Method A); M+H=445 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.91 (s, 1H), 8.11 (s, 1H), 8.08-8.02 (m, 1H), 8.01-7.97 (m, 1H), 7.74-7.69 (m, 1H), 7.50-7.48 (m, 1H), 7.27-7.16 (m, 1H), 4.15 (q, 2H), 3.85 (s, br, 3H), 3.56 (s, 3H), 2.82 (d, 3H), 1.95 (s, 3H) 1.36 (t, 3H))

Provenance & Evidence