Sodium Carbonate → HCID 86674327, compound

Participants

Reaction Conditions

Reaction Steps

N-[3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)-pyrimidin-2-amine (100 mg, 0.264 mmol), sodium carbonate (33.5 mg, 0.316 mmol), 4-(4-bromo-1,3-thiazol-2-yl)morpholine (79 mg, 0.316 mmol), 2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-tri-1-propyl-1,1′-biphenyl (7.1 mg, 0.01 mmol) and chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II) (10.5 mg, 0.013 mmol) were placed in a 4-mL vial. The vial was evacuated and back-filled with nitrogen (3×). 1,4-Dioxane (2 mL) and water (0.4 mL) were added and the reaction mixture heated to 80° C. for 16 hours. The reaction mixture was cooled to room temperature and filtered over celite with methanol (˜20 mL). Solvent evaporation gave a crude residue which was purified by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.1% trifluoroacetic acid (eluting with 40-100% MeCN), to give 20 mg (0.037 mmol, 14.2% yield) of N-{3-methyl-5-[2-(morpholin-4-yl)-1,3-thiazol-4-yl]phenyl}-4-(trifluoromethyl)pyrimidin-2-amine trifluoroacetate salt as a yellow solid. MS APCI [M+H]+ m/z 422.1. 1H NMR (500 MHz, d6-DMSO): 2.30 (s, 3H), 3.43 (t, J=4.9 Hz, 4H), 3.72 (t, J=4.9 Hz, 4H), 7.14 (s, 1H), 7.23 (d, J=4.9 Hz, 1H), 7.33 (s, 1H), 7.40 (s, 1H), 8.17 (s, 1H), 8.79 (d, J=4.9 Hz, 1H).

Provenance & Evidence