4-(2-Chloroethyl)morpholine → [4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-yl]-[3-(2-morpholin-4-yl-ethoxymethyl)-phenyl]-amine

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Reaction Steps

By alkylation of {3-[4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenyl}-methanol with 4-(2-chloro-ethyl)-morpholine. Yellow solid. Anal. RP-HPLC: tR=8.5 min (10-70% MeCN, purity>95%). 1H-NMR (DMSO-D6) δ: 2.56 (s, 3H, CH3), 2.57 (s, 3H, CH3), 2.63 (m, 2H, CH2), 3.58 (m, 4H, J=4.5 Hz, CH2x2), 4.14 (t, 2H, J=7.5 Hz, CH2), 4.58 (d, 2H, J=5.0 Hz, CH2), 5.28 (t, 1H, J=5.5 Hz, NH), 7.06 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 7.26 (m, 2H, Ph-H), 7.36 (s, 1H, Ph-H), 7.42 (m, 1H, Ph-H), 8.43 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 9.12 (sbr, 1H, Ph-H). MS (ESI+) m/z 426.46 [M+H]+ (C22H27N5O2S requires 425.55).

Provenance & Evidence