Potassium Acetate → 4-(2-fluoro-6-(morpholinomethyl)pyridin-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 4-((5-bromo-6-fluoropyridin-2-yl)methyl)morpholine (277 mg, 1.007 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (49.3 mg, 0.060 mmol), bis(pinacolato)diboron (307 mg, 1.208 mmol) and potassium acetate (198 mg, 2.014 mmol) in 2 mL of dioxane was heated in a microwave at 125° C. for 20 min. Water (0.7 mL), KOAc (100 mg), 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (504 mg, 1.309 mmol) and Am-Phos (35 mg) were added and the mixture was heated in a microwave at 102° C. for 35 min. It was diluted with 5 mL of EtOAc and washed with 1 mL of 0.5N NaOH. The EtOAc layer was concentrated and purified on a Redi-Sep pre-packed silica gel column (12 g) eluting with a gradient of 50-75% EtOAc in hexanes to give 4-(2-fluoro-6-(morpholinomethyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (115 mg, 21% yield) as a brown amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 8.60 (1H, dd, J=9.8, 1.8 Hz); 7.55 (1H, d, J=7.4 Hz); 7.24 (4H, d, J=8.2 Hz); 6.89 (4H, t, J=8.1Hz); 4.76 (4H, d, J=7.4 Hz); 3.74 (3H, s); 3.72 (3H, s); 3.60 (6H, m); 2.44 (7H, m). m/z (ESI, +ve ion) 545 (M+H)+.

Provenance & Evidence