Chloride → Methyl 6-chloro-2-(methylsulfanyl)pyrimidine-4-carboxylate

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Reaction Steps

In step a of scheme 2, reaction of diethyl diethyl oxalacetate and methylisothiourea provides the 2-methylthio-6-oxo-1,6-dihydro-pyrimidin-4-yl carboxylic acid. In step b, refluxing the carboxylic acid with tionyl chloride in an organic solvent such as tolune, followed by treatment with methanol provides the 2-methylthio-6-chloro-pyrimidin-4-yl carboxylic acid methyl ester. In step c, the methyl ester is converted to the amide using the appropriate amine, such as NHRcRd. In step d, the boronic acid derivative of Ring A (such as [Ring A]-B(OR)2, is coupled to the pyrimidine-4-carboxylic amide using a coupling reagent, such as PdCl2(dppf). The desired compound is produced via synthetic steps e and f, which are similar to steps d and e in scheme 1.

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