Methanol → 8-(3-Acetyl-5-propoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-2-methyl-4H-chromen-4-one

Participants

Reaction Steps

130 mg (0.35 mmol) of 3-acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one are suspended in THF (8 ml), and 0.39 ml (0.39 mmol) of N′″-(tert-butyl)-N,N′,N″-tris[tris(dimethylamino)phosphoranylidene]phosphorimide triamide (phosphazene base P4-t-Bu; 1 M in hexane) is added. Then 68 μl (0.41 mmol) of di-n-propyl sulfate are added to the dark red solution. The decolorized solution is stirred for 10 min, then mixed with methanol and concentrated. The residue is purified by preparative HPLC to result in 63 mg (43% of theory) of the title compound as a white solid.

Provenance & Evidence