Hydrochloric Acid → 6-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine

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Reaction Steps

To a stirred solution of 1,1-dimethylethyl [1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]carbamate (Intermediate 46) (3.00 g, 8.69 mmol) in ethanol saturated with hydrogen chloride (30 mL) was stirred overnight at room temperature. The resulting mixture was reduced under vacuum, partitioned between ethyl acetate and saturated sodium bicarbonate solution and the mixture filtered to give a solid residue. The aqueous layer was re-extracted with ethyl acetate (5×) and the combined organic layers dried with magnesium sulfate, filtered and reduced under vacuum. The residue was purified by chromatography on silica gel eluting with 50% ethyl acetate in petrol to afford a solid which was combined with the initial solid to give 6-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine (1.70 g) as a yellow solid. 1H NMR (CDCl3): δ8.35 (s, 1H), 7.53 (d, J=9.0 Hz, 2H), 7.34 (s, 1H), 6.92 (d, J=9.0 Hz, 2H), 4.33 (q, J=6.7 Hz, 1H), 3.82 (s, 3H), 1.51 (d, J=6.7 Hz, 3H).

Provenance & Evidence