1,2-Dimethoxyethane → 4-(2-Chloroquinolin-3-YL)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

A 10 mL reaction vial was charged with 4-iodo-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.36 g, 0.75 mmol, Example 115), 2-chloroquinolin-3-ylboronic acid (0.31 g, 1.50 mmol, Aldrich, St. Louis, Mo.), sodium carbonate (0.16 g, 1.50 mmol), tetrakis(triphenylphosphine)palladium (0) (43 mg, 0.04 mmol, Strem, Newburyport, Mass.), DME (4 mL), and water (1 mL). The vial was sealed and purged with argon for several minutes. The reaction mixture was stirred at 90° C. for 5 h and then allowed to cool to room. The organic phase was taken and the solvents removed under vacuum. The crude material was adsorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g) eluting with a gradient of 0% to 1% 2 M NH3.MeOH in CH2Cl2. The title compound was obtained as a yellow solid (90% pure) and used without further purification. m/z (ESI, +ve ion) 511.8 (M+H)+.

Provenance & Evidence