Trifluoroacetic acid → 4-(5-Chloro-2-(tetrahydro-2H-pyran-4-ylamino)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

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Reaction Steps

A solution of 4-(5-chloro-2-(tetrahydro-2H-pyran-4-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (190 mg, 0.339 mmol) in TFA (5000 μL, 64.9 mmol), and TfOH (100 μL, 1.126 mmol) was heated at 80° C. for 3 h. The mixture was concentrated and stirred with saturated NaHCO3 (10 mL) for 30 min. The suspension was filtered and washed with water (2×5 mL). The resulting solid was briefly rinsed with DCM (5 mL) and EtOAc (5 mL) to give the product as a yellow solid (68 mg). LCMS (ES, pos.): calcd for C14H17ClN6O: 320.1. found: 321.2 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 9.61 (d, J=7.24 Hz, 1H); 8.58 (d, J=2.15 Hz, 1H); 8.23 (d, J=2.15 Hz, 1H); 7.68 (d, J=17.41 Hz, 2H); 4.21 (br. s., 1H); 3.88 (d, J=11.54 Hz, 2H); 3.47 (t, J=10.66 Hz, 2H); 2.38 (s, 3H); 1.92 (d., J=11.932H); 1.64 (q, J=9.59 Hz, 2H).

Provenance & Evidence