Benzylamine → N2,N4-Dibenzyl-3-nitro-6-trifluoromethyl-pyridine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

A second batch of 3-Nitro-6-trifluoromethyl-pyridine-2,4-diol (11.06 g, 49.4 mmol) was dissolved in DCM (100 mL) and Et3N (13.8 ml, 98.7 mmol) was added. The mixture was cooled to 0° C. and Tf2O (16.2 ml, 98.7 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was concentrated in vacuo and the residue was dissolved in THF (100 ml). BnNH2 (16.2 ml, 148 mmol) was added and the mixture was stirred at 50° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was treated with water (100 ml) and extracted with EtOAc (200 ml). The extract was washed with brine (50 ml), dried over MgSO4 and concentrated in vacuo to give the crude (53 g). The two crudes were combined. Column chromatography through silica eluting with 95:5→90:10 Pentane:EtOAc gave the title compound (15.93 g) as a yellow solid.

Provenance & Evidence