6-Methoxy-3-pyridinylamine → HCID 66611967, compound

Participants

Reaction Steps

A solution of 6-methoxypyridin-3-amine (Sigma-Aldrich Inc., 1.405 g, 11.31 mmol) and 4-(5-chloro-2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (3.62 g, 7.54 mmol) in THF (15.00 mL) was cooled to 0° C. in an ice bath and treated with 1.0 M LiHMDS in THF (22.63 mL, 22.63 mmol). The reaction mixture was quenched with a saturated solution of NH4Cl at 0° C. and extracted with EtOAc (50 mL), dried over MgSO4, filtered and concentrated. The crude residue was re diluted with DCM and concentrated with SiO2 and chromatographed through a Redi-Sep pre-packed silica gel column on the ISCO (40 g column, 20→100% EtOAc in hexanes) to give 4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (3.77 g, 6.45 mmol, 86% yield) as a bright yellow crystalline solid. m/z (ESI, +ve ion) 584.1 (M+H)+.

Provenance & Evidence