Benzaldehyde → 1-Ethyl-6-methyl-3-phenyl-1H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione

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Reaction Conditions

Reaction Steps

Benzaldehyde (55 μl, 0.54 mmol) is added to a solution of compound 3 (115 mg, 0.54 mmol) in glacial acetic acid (2 ml) and the mixture is stirred at 10° C. for 20 min. An aqueous solution of sodium nitrite (40 mg of NaNO2 in 100 μl of water) is then added and the mixture is stirred at 10° C. for a further 30 min. The mixture is poured onto ice water and the product is extracted with ethyl acetate (3×30 ml). The organic phases are dried (Na2SO4) and the solvent is distilled off in vacuo. The residue is purified by flash chromatography (7:3, toluene/ethyl acetate). 1-Ethyl-6-methyl-3-phenyl-1H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione (44 mg, 28.8%) and 1-ethyl-4-oxy-3-phenyl-6-propyl-1H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione (41 mg, 32%) are obtained.

Provenance & Evidence