p-Toluidine → HCID 11243177, compound

Participants

Reaction Steps

To a solution of 5-trifluoromethyl-2,4-dichloropyrimidine (2 g; 9.2 mmol) in 1:1 DCE/t-BuOH (80 mL) was added Zinc chloride (11 mL of a 1M solution in ether; 1.2 eq) at 0° C. After 1 hour, 4-methylaniline (988 mg; 1 eq) was added followed by dropwise addition of a solution of triethylamine (1.03 g; 1.1 eq) in 10 mL of DCE/t-BuOH. After stirring for 1.5 hours the reaction was concentrated. Analytical HPLC analysis revealed that the crude reaction contained <5% of isomer 9. The desired product 8 was obtained as a white solid (2.25 g; 85%) following crystallization from methanol. HPLC ret. Time: 8.169 min. LRMS (M+): 288.2, 290.1.

Provenance & Evidence