Trifluoromethanesulfonic acid → 4-(5-Chloro-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

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Reaction Conditions

Reaction Steps

To a 4-(5-Chloro-2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (3.87 g, 8.06 mmol) (Example 313, Step 1) was dissolved in TFA (81 mL), trifluoromethanesulfonic acid (2.1 mL, 24 mmol) was added, and the resulting mixture was stirred at 80° C. for 2 h. The reaction mixture was then concentrated in vacuo. The residue was partitioned between EtOAc (150 mL) and sodium bicarbonate (saturated, aqueous). The organic layer was the separated, washed 2 times with 100 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0% to 40% EtOAc/hexanes) provided the title compound (51% yield). m/z (ESI, +ve ion) 240.1 (M+H)+.

Provenance & Evidence