Potassium Carbonate → 4-Anilino-5-bromo-2-{4-[3-(4-methylpiperazin-1-yl)propoxy]anilino}pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium carbonate (180 mg, 1.3 mmol), 4-anilino-5-bromo-2-(4-hydroxyanilino)pyrimidine (Method 4, 150 mg, 0.42 mmol) and 3-(4-methyl-1-piperazinyl)propyl chloride dihydrochloride (120 mg, 0.48 mmol) in DMSO (2 ml) was heated at 100° C. for 12 hours. Silica (1 g) was added and volatile material was removed by evaporation. The residue was loaded onto a Varian Mega Bond Elut column and the column was eluted with 50:50 iso-hexane: DCM (2×20 ml), DCM (2×20 ml), 2% 2M NH3/MeOH/DCM (2×20 ml), 4% 2M NH3/MeOH/DCM (2×20 ml), 6% 2M NH3/MeOH/DCM (2×20 ml) and 10% 2M NH3/MeOH/DCM (8×20 ml). Concentration of the appropriate fractions gave the product as a yellow solid (35 mg, 17%). MS (MH+): 497, 499; HPLC (RT): 2.74.

Provenance & Evidence