4-(5-(1-(Tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine → 2-(5-(4-Amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-2-methylpropan-1-ol

Participants

Reaction Conditions

Reaction Steps

Tetra(N-butyl)ammonium fluoride (1.0M in THF) (Fluka, St. Louis, Mo.; 0.432 mL, 0.432 mmol) was added to an orange solution of 4-(5-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (88.8 mg, 0.173 mmol) in THF (2.0 mL) at 0° C., and the resulting mixture was stirred at 0° C. for 10 min, then at 25° C. for 3 h. The reaction mixture was subsequently concentrated onto silica gel and chromatographically purified (silica gel, 0 to 100% EtOAc/hexanes) to provide 2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-2-methylpropan-1-ol (44.0 mg, 0.110 mmol, 63.7% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 11.87 (s, 1H), 8.81 (d, J=2.7 Hz, 1H), 8.37-8.43 (m, 3H), 7.86 (br. s., 1H), 7.72 (br. s., 1H), 4.75 (br. s., 1H), 3.93 (s, 3H), 3.43 (s, 2H), 2.44 (s, 3H), 1.27 (s, 6H). 19F NMR (377 MHz, d6-DMSO) δ −139.89 to −139.79 (m, 1F). m/z (ESI, +ve) 400.3 (M+H)+.

Provenance & Evidence