Reaction Steps
By hydrolysis of 1-(4-{4-[4-(4-Methyl-2-methylamino-thiazol-5-yl)-pyrimidin-2-ylamino]-phenyl}-piperazin-1-yl)-ethanone in 2 M aq HCl. Yellow solid. Anal. RP-HPLC: tR=8.8 min (10-70% MeCN, purity >95%). 1H-NMR (DMSO-d6) δ: 2.45 (3, 3H, CH3), 2.83 (t, 4H, J=5.9 Hz, CH2), 2.85 (d, 3H, J=4.9 Hz, CH2), 2.95 (t, 4H, J=4.9 Hz, CH2), 6.81 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 6.85 (d, 2H, J=9.3 Hz, Ph-H), 7.58 (d, 2H, J=8.8 Hz, Ph-H), 7.99 (m, 1H, NH), 8.26 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 9.14 (brs, 1H). N-{3-[4-(4-Methyl-2-methylamino-thiazol-5-yl)-pyrimidin-2-ylamino]-benzyl}-acetamide [63]. By condensation of 3-dimethylamino-1-(2-methylamino-4-methyl-thiazol-5-yl)-propenone and N-(3-guanidino-benzyl)-acetamide nitrate. Yellow solid. Mp 253-255° C. Anal. RP-HPLC: tR=11.3 min (10-70% MeCN, purity >95%): 1H NMR (DMSO): δ 1.86 (s, 3H, CH3), 2.46 (s, 3H, CH3), 2.85 (s, 2H, CH2), 3.09 (s, 3H, CH3), 6.82 (d, 1H, J=8.0 Hz, ph-H), 6.88 (d, 1H, J=5.5 Hz, pyrimidinyl-H), 7.2 (t, 1H, J=8.0 Hz, Ph-H), 7.60 (d, 1H, J=8.0 Hz, Ph-H), 7.73 (s, 1H, Ph-H), and 8.32 (d, 1H, J=5.5 Hz, pyrimidinyl-H). MS (ESI+) m/z 391.55 [M+Na] (C18H20N6OSNa requires 391.46).
