1,4-Benzodioxan-6-ylamine → N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-hydro xy-2-phenylethyl)-2,4-pyrimidinediamine

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Reaction Steps

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(2-hydroxy-2-phenylethyl)-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(2-hydroxy-2-phenylethyl)-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.79 (s, 1H), 7.48 (m, 5H), 6.89-6.71 (m, 3H), 5.41-5.38, 4.97 (dd, 1H, J=3.6 and 7.5 Hz), 4.28-4.22 (m, 4H), 3.88 (ddd, 1H, J=4.2, 7.2, and 14.1), 3.64-3.55 (m, 1H); 19F NMR (CDCl3): −47910; LCMS: ret. time: 20.47 min.; purity: 88%; MS (m/e): 383 (MH+).

Provenance & Evidence