Succinic anhydride → Succinic acid mono-{4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl}-ester

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Reaction Steps

To a stirred suspension of the title compound of Example 44 (0.300 g, 0.809 mmol) and succinic anhydride (0.097 g, 0.971 mmol) in chloroform (10 ml) was added 4-dimethyl-amino-pyridine (0.138 g, 1.13 mmol). After stirring for 16 hours, the mixture was concentrated under reduced pressure. Water (10 ml) was added and the mixture was adjusted to pH 2 by addition of aqueous potassium hydrogen sulfate solution (0.5 M). The solid was filtered and dried under reduced pressure to provide the title compound (0.381 g, 81% yield). 1H NMR (DMSO-d6) δ1.38 (t, 3H, J=6.9 Hz, CH3), 2.48-2.50 (m, 2H, CH2), 2.50-2.52 (m, 2H, CH2), 4.13 (q, 2H, J=6.9 Hz, CH2), 5.05 (s, 2H, CH2), 6.28 (s, 2H, NH2), 6.79 (s, 1H, Ar), 7.14 (d, 1H, J=8.9 Hz, Ar), 7.29 (d, 2H, J=8.9 Hz, Ar), 7.41 (dd, 1H, J=8.9 Hz, 2.9 Hz, Ar), 7.71 (d, 2H, J=8.5 Hz, Ar), 7.93 (s, 1H, Ar), 9.22 (s, 1H, NH), 12.05 (s, 1H, COOH).

Provenance & Evidence