1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 67209483, compound

Participants

Reaction Conditions

Reaction Steps

4-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-6-[1-(3-fluorophenyl)-1-methoxymethoxyethyl]pyrimidin-2-ylamine (0.249 g, 0.395 mmol) is dissolved in DMF (7 ml), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.164 g, 0.790 mmol) and Pd[PPh3]4 (0.046 mg, 0.040 mmol) are added, the reaction solution is flushed with nitrogen for 5 min, 2N Na2CO3 solution (1.5 ml) is subsequently added. The mixture is stirred at 130° C. for 1 h. The mixture is cooled to room temperature, ethyl acetate is added, and the organic phase is extracted three times with water, the aqueous phase is separated off, and the organic phase is dried over sodium sulfate. The solid is filtered off, and the residue is evaporated in vacuo. The residue is purified by RP-HPLC, giving 4-[1-(3-fluorophenyl)-1-methoxymethoxyethyl]-6-[2-(1-methyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]pyrimidin-2-ylamine (“A2”), (HPLC/MS Rt=1.72 min, [M+H] 475); 1H-NMR [DMSO-d6]: δ [ppm]=12.72 (br, 1H), 8.72 (s, 1H), 8.49 (m, 1H), 8.33 (s, 1H), 8.31 (s, 1H), 8.11 (s, 1H), 7.43 (m, 1H), 7.32 (m, 2H), 7.13 (m, 1H), 4.79 (s, 2H), 3.95 (s, 3H), 3.37 (s, 3H), 1.98 (s, 3H);

Provenance & Evidence