Diisopropylethylamine → 2-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide

Participants

Reaction Steps

A solution of 2,4,5-trichloropyrimidine (1.0 g, 5.4 mmol) and 2-amino-N-methylbenzamide (0.98 g, 6.5 mmol) in THF (5.0 mL) was charged with DIPEA (1.42 mL, 8.18 mmol) and the mixture allowed to stir at rt for 16 h. The reaction was quenched with NaHCO3 (10 mL) and extracted with EtOAc (15 mL). The organic layer was washed with brine (10 mL), dried over NaSO4, filtered, and concentrated in vacuo to yield a yellow solid which was recrystallized from EtOAc to afford 422 mg of 2-[(2,5-dichloropyrimidin-4-yl)amino]-N-methylbenzamide (yield: 26% yield*). Further material could be recovered from the mother liquors if desired. 1H NMR (CD3OD, 400 MHz): δ=2.93 (s, 3 H), 7.21 (td, J=7.64, 1.14 Hz, 1 H), 7.56 (ddd, J=8.53, 7.26, 1.64 Hz, 1 H), 7.71 (dd, J=7.83, 1.26 Hz, 1 H), 8.30 (s, 1 H) 8.63 (dd, J=8.59, 0.76 Hz, 1 H). MS (ES+): m/z 296.90 [MH+] (ZQ3, polar—5 min).

Provenance & Evidence