Ethylamine → 4-(4-Ethylaminopyrimidin-6-yloxy)aniline

Participants

Reaction Steps

A suspension of 4-(6-chloro-pyrimidin-4-yl-oxy)-aniline (Stage 21.1; 5.0 g, 22.6 mmol) in ethylamine dissolved in ethanol (≈35%; 5 ml) under Nratmosphere is stirred for 16 h at rt. Then the resulting brown solution is diluted with water and AcOEt, the aqueous layer separated off and extracted twice with AcOEt. The organic phases are washed with 3 portions of water and brine, dried (Na2SO4) and concentrated. Re-crystallisaton from boiling AcOEt gives the title compound: m.p.: 143-145° C.; 1H-NMR (CDCl3): 8.24 (s, 1H), 7.24 (s, HN), 6.91 (d, 2H), 6.69 (d, 2H), 5.63 (s, 1H), 4.97 (s, H2N), 3.25 (m, 2H), 1.25 (t, 3H). More product can be isolated from the filtrate of the re-crystallization by column chromatography (SiO2; AcOEt→AcOEt/EtOH 19:1).

Provenance & Evidence