Methanol → HCID 58999602, compound

Participants

Reaction Steps

In a round bottom flask, 7-Benzyl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimdine-4-carboxylic acid(adamantan-1-ylmethyl)-amide(1.15 g, 2.74 mmol) was dissolved in glacial acetic acid (10 mL) with stirring and 10% Pd/C (417 mg) was added. The suspension was stirred under an atmosphere of H2 for 16 h. By LCMS and TLC (DCM:MeOH::20:1), no starting material appeared to be present. The desired m/z was observed at 327.3 (M+H). The reaction mixture was then filtered through a pad of celite. The filtrate was concentrated. The resulting oil was re-dissolved in EtOAc (50 mL) with stirring. A 10% NaOH solution (50 mL) was added. The mixture was stirred at RT for 1 h. The layers were separated and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were filtered through a Horizon Technologies DryDisk and concentrated. The crude oil was chromatographed using DCM/MeOH (0-30% gradient) as elutant affording 0.133 g of the title compound.

Provenance & Evidence