Sodium Carbonate Monohydrate → HCID 178476635, compound

Participants

Reaction Steps

A mixture of 3-phenyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,5-pyrrolidinedione (0.35 g, 0.00093 mol), cis-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.34 g, 0.000773 mol), tetrakis-(triphenylphosphine)palladium (0.053 g, 0.000046 mol) and sodium carbonate monohydrate (0.24 g, 0.00193 mol) was heated in a mixture of ethylene glycol dimethyl ether (14 mL) and water (7 mL) at 80° C. for sixteen hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and solvents were removed under the reduced pressure. The residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield cis-4-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}anilino)-4-oxo-2-phenylbutanoic acid acetate (0.150 g, 0.000233 mol) and cis-4-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}anilino)-4-oxo-3-phenylbutanoic acid acetate (0.11 g, 0.000171 mol) both as white solids.

Provenance & Evidence