Potassium Acetate → 4-(2-fluoro-6-methylpyridin-3-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 2-fluoro-6-picoline-3-boronic acid (Asynchem Laboratories, Inc.) (430 mg, 2.77 mmol), 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (970 mg, 2.52), potassium acetate (742 mg, 7.56 mmol) and bis(di-tert-butyl (4-dimethylaminophenyl)phosphine)dichloropalladium(II) (Aldrich) (89 mg, 0.126 mmol) in 8 mL of dioxane and 2 mL of water was heated in a microwave at 110° C. for 30 min. It was diluted with EtOAc and washed with 1 N NaOH. The organic layer was dried and concentrated. The residue was purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 25-50% EtOAc in hexanes to give 4-(2-fluoro-6-methylpyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (939 mg, 2.043 mmol, 81% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 8.53 (1H, m); 7.37 (1H, d, J=6.5 Hz); 7.24 (4H, dd, J=8.6, 1.2 Hz); 6.89 (4H, t, J=Hz); 4.75 (4H, d, J=6.5 Hz); 3.74 (3H, s); 3.72 (s, 3H); 2.51 (3H, s); 2.45 (3H, s). m/z (ESI, +ve ion) 460 (M+H)+.

Provenance & Evidence