1,2-Dimethoxyethane → HCID 60155703, compound

Participants

Reaction Conditions

Reaction Steps

A 20 mL reaction vial was charged with 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.31 g, 1.42 mmol, Oakwood Products, West Columbia, S.C.), tetrakis(triphenylphosphine)palladium (0) (63 mg, 0.06 mmol, Newburyport, Mass.), 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.42 g, 1.10 mmol), sodium carbonate (0.29 g, 2.73 mmol), DME (5 mL), and water (1.5 mL). The vial was sealed and purged with argon for several minutes. The reaction mixture was stirred at 90° C. for 2 h and allowed to cool to room temperature. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (20 mL). The organic extract was washed with water and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was adsorbed ontodsilica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g) eluting with a gradient of 0% to 1% MeOH in CH2Cl2 to give the title compound as a light yellow oil. m/z (ESI, +ve ion) 441.9 (M+H)+.

Provenance & Evidence