Triphenylphosphine → 5-(5-Methoxy-pyridin-2-ylmethoxy)-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-hydroxy-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (described in preparation 5a of WO 08/022,979, 705 mg, 3.59 mmol) and (5-methoxy-pyridin-2-yl)-methanol (Milestone Pharmtech, 500 mg, 3.59 mmol) in THF (10 mL) is added polymer-bound triphenylphosphine (2.40 g, 3 mmol/g, 7.2 mmol). After cooling to 0° C., diisopropyl azodicarboxylate (1.42 mL, 7.2 mmol) is added slowly. Afterwards, the reaction mixture is stirred for 3 h at room temperature. The reaction mixture is filtered and the solvent is evaporated. The residue is purified via reverse phase HPLC chromatography (Waters XBridge 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH).

Provenance & Evidence