Trifluoromethanesulfonic acid → HCID 59548472, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(5-(3,6-dihydro-2H-pyran-4-yl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (140 mg, 0.215 mmol) in 3 mL of TFA was treated with 0.15 mL of trifluoromethanesulfonic acid and heated at 80° C. in an oil bath for 3 h. It was concentrated and the dark residue was stirred in 15 mL of EtOAc then treated with 5 mL of 1 N NaOH. The aqueous layer was extracted with 2×10 mL of DCM. The combined EtOAc extracts and DCM extracts were concentrated. The residue was purified on a silica gel column and eluted with 35-100% EtOAc in DCM to give 4-(5-(3,6-dihydro-2H-pyran-4-yl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (70 mg, 79% yield) as a yellow crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.95 (s, 1H), 8.85 (d, J=2.6 Hz, 1H), 8.49 (d, J=2.5 Hz, 1H), 8.41-8.35 (m, 2H), 7.91 (br., 1H), 7.76 (br., 1H), 6.24 (m, 1H), 4.24 (m, 2H), 3.94 (s, 3H), 3.84 (m, 2H), 2.45 (s, 5H). m/z (ESI, positive ion) 410.0 (M+H)+.

Provenance & Evidence