Hydrazine hydrate (1:1) → 3-(2-aminoethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Participants

Reaction Steps

A mixture of 2-{2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}-1H-isoindole-1,3(2H)-dione (prepared as described in Example 90/350 mg, 0.65 mmol) and hydrazine monohydrate (63111) in ethanol (2 ml) was refluxed overnight. After evaporation of the solvent, the crude material was purified by preparative HPLC (column beta-basic, Hypercil 5 μm, 21×100 mm) eluting with a mixture of water and acetonitrile containing 2g/l of ammonium carbonate (gradient) to give the title compound (184 mg, 69%); NMR Spectrum: 2.94 (t, 2H), 4.25 (t, 2H), 5.29 (s, 2H), 7.23 (d, 1H), 7.37 (t, 1H), 7.53-7.58 (m, 2H), 7.85-7.90 (m, 2H), 8.26 (s, 1H), 8.60 (br s, 2H). Mass Spectrum: 412 (MH+).

Provenance & Evidence