Thionyl Chloride → 4,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

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Reaction Conditions

Reaction Steps

To 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde oxime (2.38 g, 10 mmol) was added SOCl2 (21.8 mL, 0.30 mol) slowly at room temperature. The solution was then heated at 75° C. for about 3 hours before it was concentrated under vacuum. The residue SOCl2 was removed by evaporation with toluene (5 mL) under vacuum. The resulting solid was washed with EtOH/H2O (10 mL, 1:1) to afford 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbonitrile (2.04 g, 93%). LC-MS m/z 220 (M+H)+1.99 minute; 1H-NMR (CDCl3) δ 2.64(3H).

Provenance & Evidence