Triethylamine → (E)-2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)vinyl)quinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methyl-6-vinylpyrimidine (1-3) (200 mg, 0.93 mmol, 1.0 eq.) in degassed DMF (4.0 mL) was added 2-chloroquinoline (148 mg, 0.93 mmol, 1.0 eq.) followed by palladium acetate (32.0 mg, 47.5 mol, 0.050 eq.) and triethylamine (1.20 mL, 4.65 mmol, 5.0 eq.). The reaction was heated at 100° C. for 48 hours and cooled to room temperature. The reaction was quenched by the addition of water (5.0 mL) and ethyl acetate (5.0 mL) was added and the mixture was filtered through Celite. The organic layer was separated and the aqueous layer was washed with ethyl acetate (2×5.0 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by silica gel chromatography (10-40% ethyl acetate in hexanes) to afford (E)-2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)vinyl)quinoline (1-4) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 8.19 (br d, 1H, J=8.5 Hz), 8.13 (d, 1H, J=16.0 Hz), 8.11 (br d, 1H, J=8.3 Hz), 7.87 (br s, 111), 7.81 (br dd, 1H, J=8.0, 1.0 Hz), 7.78-7.68 (m, 3H), 7.55 (ddd, 1H, J=8.0, 7.0, 1.0 Hz), 2.94 (s, 3H), 2.77 (s, 3H), 2.44 (s, 3H). LRMS mz (M+H+) 343 found, 343 required. m.p. 153-155° C.

Provenance & Evidence