HCID 66611464, compound → HCID 59548445, compound

Participants

Reaction Steps

A solution of 4-(2-(3-fluoro-4-methoxyphenylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.1253 g, 0.221 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight. The TFA was removed in vacuo and the residue was treated with a saturated solution of NaHCO3. The mixture was extracted with DCM (3×15 mL) and concentrated. The crude brown oil was dissolved in 2.5 mL of DMSO and purified by reversed phase chromatography (Gilson, 10-90% CH3CN in water with NH4OH additive: 0.1% v/v in each solvent). The fractions were concentrated in a Genevac Series II System to give 4-(2-(3-fluoro-4-methoxyphenylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (3.3 mg, 10.11 μmol, 4.57% yield) as a yellow amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.91 (s, 1H); 8.77 (dd, J=7.8, 2.0 Hz, 1H); 8.35 (dd, J=4.7, 2.0 Hz, 1H); 7.94 (dd, J=14.2, 2.6 Hz, 1H); 7.48-7.53 (m, 1H); 7.11 (t, J=9.4 Hz, 1H); 6.90 (dd, J=7.8, 4.7 Hz, 1H); 3.82 (s, 3H); 2.43 (s, 3H). m/z (ESI, +ve ion) 327.1 (M+H)+.

Provenance & Evidence