Sodium Carbonate → 4-(5-(3,6-Dihydro-2H-pyran-4-YL)-2-fluoropyridin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(5-chloro-2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (2.0 g, 4.17 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Frontier Scientific) (1.051 g, 5.00 mmol), Pd2(dba)3 (0.191 g, 0.208 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.199 g, 0.417 mmol) and 2 N Na2CO3 (5.21 mL, 10.42 mmol) in 10 mL of dioxane was heated in a microwave at 130° C. for 30 min. The reaction mixture was partitioned between 10 mL of 0.5 N NaOH and 50 mL of EtOAc. The organic layer was separated and washed with brine, dried and concentrated. The residue was purified on a silica gel column and eluted with 25 to 75% EtOAc in hexanes to give the title compound (1.19 g, 54% yield) as an off white crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.51-8.47 (m, 2H), 7.24 (t, J=9.2 Hz, 4H), 6.90 (m, 4H), 6.38 (m, 1H), 4.78 (s, 2H), 4.76 (s, 2H), 4.24 (d, J=2.7 Hz, 2H), 3.84 (m, 2H), 3.74 (s, 3H), 3.72 (s, 3H), 2.51 (m, 2H), 2.47 (s, 3H). m/z (ESI, positive ion) 528.0 (M+H)+.

Provenance & Evidence