Sodium Carbonate → Tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)piperidine-1-carboxylate

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Reaction Conditions

Reaction Steps

tert-Butyl 4-methylenepiperidine-1-carboxylate (0.117 g, 0.592 mmol) was treated with 9-BBN (0.5 M in THF, 1.183 mL, 0.592 mmol) and the mixture was heated at reflux for 4 h. After cooling, the resulting solution was transferred into a stirred mixture of 4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.288 g, 0.493 mmol), Pd2(dba)3 (0.023 g, 0.025 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.024 g, 0.049 mmol), and Na2CO3 (0.131 g, 1.233 mmol) in 1,4-dioxane (1.0 mL) and water (0.25 mL). The mixture was sealed and heated under microwave at 140° C. for 30 min. After cooling, the resulting mixture was passed through a short path of Celite® (diatomaceous earth), washing with EtOAc (3×10 mL). The combined organic phases were concentrated and purified by flash chromatography (short column, SiO2, pure hexanes→30% EtOAc in hexanes) to give tert-butyl 4-((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)piperidine-1-carboxylate (0.261 g, 0.349 mmol, 70.9% yield) as a sticky yellow syrup. m/z (ESI, +ve ion) 747.2 (M+H)+.

Provenance & Evidence