Uracil → 2-Methylthio-5-(3-pyridyl)methoxy-4-pyrimidone

Participants

Reaction Steps

Following the above procedure, 3.03 g. of sodium were suspended in anhydrous ether in a nitrogen atmosphere. 5.93 g. of ethyl formate plus 14.1 g. of ethyl 3-pyridylmethoxyacetate were added. The product of the reaction, ethyl formyl-(3-pyridylmethoxy)acetate as the sodium salt, was suspended in 175 ml. of ethanol and 5.8 g. of thiourea were added. The product of this reaction, 5-(3-pyridylmethoxy)-2-thiouracil, melted at 243°-245° C.; weight=10.4 g. 9.9 g. of the uracil were slurried in 80 ml. of ethanol. A solution containing 1.78 g. of sodium hydroxide and 38 ml. of water was added followed by 4.86 g. of methyl iodide. 1.46 g. of 2-methylthio-5-(3-pyridyl)methoxy-4-pyrimidone were obtained melting at 186°-187° C.

Provenance & Evidence