4-Methyl-2-(methylsulfanyl)pyrimidine

Chemical Properties

Colorless to yellow to red liquid

Uses

4-Methyl-2-(methylthio)pyrimidine is used as a reagent to prepare pyrazolopyrimidines and pyrazolotriazines, both of which display potent activity against herpes viruses. 4-Methyl-2-(methylthio)pyrimidine is also used as a starting material to synthesize 4-substituted-2-aminopyrimidines (e.g. 2-amino-4-ethylpyridine [A609500]), novel c-Jun N-terminal kinase (JNK) inhibitors.

Synthesis

To an aqueous (120 mL) solution of NaOH (7.46 g, 186.4 mmol) under argon atmosphere, 4-methylpyrimidine-2-thiolate (13.78 g, 84.7 mmol) was added, followed by the dropwise addition of into iodomethane (13.23 g, 93.2 mmol). The solution was stirred at room temperature for 2 hours and then CH2Cl2(2x) was used to Extraction. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by silica gel chromatography using a hexane-EtOAc mixture of increased polarity as eluent to yield 10.26 g of the desired compound (yield: 86%).