A mixture of 2-chloro-4,6-dimorpholine-1,3,5-triazine (2.30 g, 0.105 mol) and pinacol ester of 4-aminophenylboronic acid (25.7 g, 0.117 mol) was heated and refluxed for 5 h in the presence of sodium carbonate (23 g, 0.21 mol) and tetrakis(triphenylphosphine)palladium (1 g, 0.5 wt%) in a mixture of water (150 mL) and dimethoxyethane ( DME, 450 mL) in a solvent mixture of water (150 mL) and dimethoxyethane (DME, 450 mL) was heated to reflux for 5 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through filter paper. The organic layer in the filtrate was separated, washed with brine and concentrated. The concentrated residue was dissolved in dichloromethane, washed again with brine, dried over anhydrous sodium sulfate and concentrated. The resulting solid was ground with ether, filtered and air dried to give the beige solid product 4-(4,6-dimorpholino-1,3,5-triazin-2-yl)aniline (31.5 g, 0.092 mol) in 88% yield. Mass spectrometry analysis showed a molecular ion peak of 343.1 (M + H)+ for the target compound.
