2-Amino-4-chloro-6-methylpyrimidine → 4-Chloro-5-iodo-6-methylpyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-4-chloro-6-methylpyrimidine (Aldrich, 10 g, 70 mmol) in acetonitrile (100 mL) and MeOH (140 mL) was added N-iodosuccinimide (Aldrich, 24 g, 105 mmol) at room temperature. The reaction mixture was heated to 60° C. for 5 h under a nitrogen atmosphere. After the reaction was complete, by monitoring LC/MS, it was allowed to cool to room temperature. The reaction mixture was put on a rotary evaporator and the solvent was evaporated to the half of its original volume. A precipitate was formed by addition of diethyl ether (200 mL). The precipitate was collected by vacuum filtration to afford (15.7 g, 83% yield) of the 4-chloro-5-iodo-6-methylpyrimidin-2-amine; MS (EI) for C5H5ClIN3 (272.65, M+2): analytical HPLC purity >97%.

Provenance & Evidence