3,4,5-Trimethoxyaniline → N4-(5-tert-butylisoxazol-3-yl)-N2-(3,4,5-trimethoxy-phenyl)-pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-chloropyrimidin-4-yl)-(5-tert-butyl-isoxazol-3-yl)amine (50 mg 0.198 mmol Step A) and 3,4,5-trimethoxyaniline (36.2 mg 0.198 mmol) was suspended in 0.15 mL of a 2M solution of Et3N-TFA in DMSO (stock solution prepared by combining 1.28 g of Et3N-TFA and 3 mL of DMSO) in a sealed tube. The resulting mixture was heated at 100° C. for 4 h, cooled to RT, diluted with CH2C12 (attempted crystallization), concentrated and purified via preparative HPLC to give N4-(5-tert-butylisoxazol-3-yl)-N2-(3,4,5-trimethoxy-phenyl)-pyrimidine-2,4-diamine as a green-gray amorphous solid. MS m/z=400. Calc'd for C20H25N5O4— 399.19.

Provenance & Evidence