Ammonia → Methyl 4-(6-carbamoyl-3-(methylthio)-1,2,4-triazin-5-ylamino)benzoate

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Reaction Steps

To ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (1) (350 mg, 1.50 mmol) in acetonitrile (10 mL) was added methyl 4-aminobenzoate (340 mg, 2.25 mmol) and then diisopropylethylamine (DIEA, 0.39 mL, 2.25 mmol). The mixture was stirred at RT for 3 h. To the mixture was then added ammonia (7.0 N solution in methanol, 30 mL). The mixture was stirred overnight. The solid was isolated by filtration, washed with a minimum amount of cold acetonitrile and then washed with hexane. The solid was dried in a vacuum oven to afford methyl 4-(6-carbamoyl-3-(methylthio)-1,2,4-triazin-5-ylamino)benzoate (2) (348 mg, 73% yield) in high purity.

Provenance & Evidence