Sodium → 4-[2-(4-Trifluoromethylphenyl)-pyrimidin-4-yl]-phenylamine

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Reaction Steps

4-(4-Nitrophenyl)-2-(4-trifluoromethylphenyl)-pyrimidine. To sodium metal (82.7 mg, 3.60 mmol) dissolved in absolute EtOH (3 mL) was added 4-trifluoromethylbenzamidine hydrochloride dihydrate (938 mg, 3.60 mmol) followed by EtOH (4 mL). After 30 min, 3-dimethylamino-1-(4-nitrophenyl)-propenone (498 mg, 2.26 mmol) was added, and the mixture was heated at reflux approximately 66 h and was then allowed to cool. The mixture was concentrated to a tan solid which was triturated under saturated sodium bicarbonate. The solid was collected and air dried to give 937 mg. It was then dissolved in chloroform/EtOAc and was passed over silica gel eluting with 7:3 chloroform/EtOAc to afford the title compound (710 mg, 91%): mp 175-176.5° C.; 1H NMR δ 9.01 (d, J=5.3 Hz, 1H), 8.73 (d, J=8.2 Hz, 2H), 8.43 (s, 4H), 7.82 (d, J=8.1 Hz, 2H), 7.76 (d, J=5.2 Hz, 1H); EIMS m/z 345 (M+, 100), 299 (57). Anal. Calcd. for C17H10F3N3O2: C, 59.13; H, 2.92; N, 12.17. Found: C, 58.82; H, 2.63; N, 11.98.

Provenance & Evidence