Hydrochloric Acid → 5,6-dimethyl-N4-(piperidin-4-yl)-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

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Reaction Steps

tert-Butyl 4-({5,6-dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4-yl}amino)piperidine-1-carboxylate (100 mg, 0.24 mmol, Example 82) was suspended in a solution of 3 M hydrogen chloride in dioxane (10 mL). The reaction mixture was stirred at ambient temperature overnight, and then the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel eluted with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1) to afford the titled compound as a light-grey solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.25-1.32 (m, 2H), 1.84-1.92 (m, 5H), 2.25 (s, 3H), 12.43 (bs, 1H), 2.60-2.65 (m, 2H), 3.02-3.08 (m, 2H), 3.985-3.94 (m, 1H), 4.25 (d, J=8.3 Hz, 2H), 4.68 (d, J=5.3 Hz, 2H), 5.59 (bs, 1H), 7.12 (t, J=4.6 Hz, 1H), 7.36 (d, J=8.1 Hz, 1H), 7.60 (t, J=6.4 Hz, 1H), 8.54 (d, J=4.2 Hz, 1H); MS (ESI) m/z 313.2 (M+1)+.

Provenance & Evidence