6-Methoxy-3-pyridinylamine → 3-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)-N-(6-methoxypyridin-3-YL)quinolin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-amino-2-methoxypyridine (0.08 mL, 0.61 mmol, Aldrich, St. Louis, Mo.) and 4-(2-chloroquinolin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (210 mg, 0.410 mmol) in THF (3 mL) was cooled to 0° C. and LiHMDS (1 M in THF, 1.23 mL, 1.23 mmol) was added. The reaction mixture was stirred at 0° C. for 1 h, diluted with an aqueous satd solution of NH4Cl (5 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, and the residue was adsorbed onto a plug of silica gel. Purification by chromatography through a Redi-Sep pre-packed silica gel column (12 g) eluting with a gradient of 2% to 3% 2 M NH3.MeOH in CH2Cl2 gave the title compound as an orange solid (65% pure) that was used without further purification. m/z (ESI, +ve ion) 599.8 (M+H)+.

Provenance & Evidence