Acetic Acid → HCID 66735705, compound

Participants

Reaction Steps

To crude 5-(1-aminoethyl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.6 g) in DCE (20 ml) and Ethanol (20 ml) was added tetrahydro-4H-pyran-4-one (0.6 ml, 7 mmol) followed by AcOH (0.08 ml, 1.4 mmol). After stirring for 30 minutes at room temperature, NaBH3CN (0.18 g, 2.8 mmol) was added and stirring was continued further for 30 minutes more. LC/MS showed no starting material (M.W=437) remaining. After the solvent was rotoevaporated, the crude was dissolved with DCM (60 ml), washed with sat. NaHCO3 (1×5 ml), water (1×5 ml), brine (1×5 ml), dried over MgSO4. Solvent was removed in vacuo and the residue was purified by column chromatography on silica gel. Elution with MeOH/EtOAC (0-20%) gave desired product, 5-(1-(tetrahydro-2H-pyran-4-ylamino)ethyl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.2 g, 27%).

Provenance & Evidence