Phosphorus oxychloride → 4-Chloro-5-(4-fluorophenyl)-2-methylthio-6-(4-pyridyl)pyrimidine

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Reaction Steps

5-(4-fluorophenyl)-3-methyl-2-methylthio-6-(4-pyridyl)-3H-pyrimidin-4-one (0.327 g, 1 mmol) and 5 ml of POCl3 in a 15-ml r.b.flask with a stir bar was stirred at 120° C. for 16 h. The remaining POCL3 was evaporated in vacuo. The dark brown residue was mixed with ice-water. The resulting acidic dark brown solution was neutralized to pH 7-8 with sat'd NaHCO3 and extracted by EtOAc (2×10 ml). The combined organic layers were washed with brine (10 ml) and dried over Na2SO4. 4-chloro-5-(4-fluorophenyl)-2-methylthio-6-(4-pyridyl)pyrimidine was isolated by flash chromatography with 50% EtOAc in hexane; MS: m/z (M+H)+ 332; C16H11ClFN3S requir.331.8.

Provenance & Evidence