Cesium carbonate → 4-(3-Chloropyridin-4-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

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Reaction Conditions

Reaction Steps

A mixture of 4-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (306 mg, 0.642 mmol), 3-chloropyridine-4-boronic acid (101 mg, 0.642 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) (52.4 mg, 0.064 mmol) and cesium carbonate (251 mg, 0.770 mmol) in dioxane (6 mL) and water (1 mL) was stirred at 90° C. for 1 h. The mixture was cooled down to room temperature. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow glass. The crude product was purified by silica gel chromatography eluting with 50% EtOAc/hexanes to give the product as a glass. 1H NMR (300 MHz, CDCl3) δ 8.69 (s, 1H); 8.58 (d, J=4.97 Hz, 1H); 7.71 (d, J=4.82 Hz, 1H); 7.10-7.26 (m, 4H); 6.86 (t, J=8.77 Hz, 4H); 4.80 (s, 4H); 3.81 (s, 3H); 3.80 (s, 3H); 2.56 (s, 3H). m/z (ESI, +ve ion) 462.0 (M+H)+.

Provenance & Evidence