N,N-dimethyl-p-phenylenediamine → N-(4-Chloro-5-trifluoromethyl-pyrimidin-2-yl)-N',N'-dimethyl-benzene-1,4-diamine

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Reaction Steps

To a solution of 5-trifluoromethyl-2,4-dichloropyrimidine (500 mg; 2.3 mmol) in 1:1 DCE/t-BuOH (20 mL) was added Zinc chloride (5.1 mL of a 1 M solution in ether; 2.2 eq) at 0° C. After 1 hour, N,N-dimethyl-1,4-phenylenediamine (313 mg; 1 eq) was added followed by dropwise addition of a solution of triethylamine (279 mg; 1.1 eq) in 5 mL of DCE/t-BuOH. After stirring for 24 hours the reaction was concentrated. The product was obtained as a pale green solid (531 mg; 73%) following crystallization from 25% H2O/methanol. 1H NMR (DMSO-d6, 400 MHz) δ 2.83 (s, 6H), 6.69 (m, 2H), 7.39 (m, 2H), 8.65 (s, 1H), 10.32 (s, 1H); 13C NMR (CDCl3, 100 MHz) δ 161.3, 158.8 (br), 158.5 (br), 148.3, 128.2, 123.8 (q, J=268 Hz), 123.0, 113.1, 110.8 (br), 41.0; HPLC ret. time: 7.901 min. LRMS (M+) 317.3, 319.3.

Provenance & Evidence