Trifluoroacetic acid → 4-(2-(5-Fluoro-6-methoxypyridin-3-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

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Reaction Conditions

Reaction Steps

4-(2-(5-Fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (232 mg, 0.409 mmol) was treated with TFA (8.0 mL) (Aldrich) and heated at 75° C. with a reflux condenser for 17 h. The TFA was removed in vacuo and the crude product was treated with 2 M NH3 in MeOH resulting in a suspension that was filtered and washed with water to give the desired product in ca. 80% purity. It was then resuspended in MeOH and filtered and washed with 1 N NaOH (aq), MeOH and hexanes and dried to give an olive-colored amorphous solid. It was further purified on the ISCO (12 g column, 1-25% MeOH in DCM) to give 4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (68.6 mg, 0.210 mmol, 51.3% yield) as a fibrous, yellow amorphous solid. m/z (ESI, +ve ion) 328.1 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.95 (1H, s); 8.80 (1H, dd, J=7.8, 2.0 Hz); 8.42 (1H, d, J=2.3 Hz); 8.33-8.40 (2H, m); 7.91 (1H, br. s.); 7.77 (1H, br. s.); 6.94 (1H, dd, J=7.8, 4.7 Hz); 3.94 (3H, s); 2.43 (3H, s).

Provenance & Evidence