Diisopropylamine → 3-Methyl-1-(2-(methylthio)pyrimidin-4-yl)butan-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (10.1 mL, 71.8 mmol) in anhydrous THF (50 mL) is added n-butyllithum (33.6 mL of an 1.6M in hexane) dropwise at 0° C. After 30 min at 0° C., 4-methyl-2-(methylthio)pyrimidine (5 mL, 35.9 mmol) is added. The resulting mixture is stirred at 0° C. for 30 min. After the addition of methyl isobutyrate (4.3 mL, 37.7 mmol) at 0° C., the reaction mixture is stirred overnight. The reaction mixture is quenched with acetic acid at 0° C., diluted with water, and extracted with ethyl ether. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, EtOAc/heptane 7:93 to 40:60) to give 4.3 g of 3-methyl-1-(2-methylsulfanyl-pyrimidin-4-yl)-butan-2-one.

Provenance & Evidence