2-Amino-4-chloro-6-methylpyrimidine → 4-Chloro-5-iodo-6-methylpyrimidin-2-amine
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[I:10]N1C(=O)CCC1=O>C(#N)C.CO>[Cl:8][C:6]1[C:5]([I:10])=[C:4]([CH3:9])[N:3]=[C:2]([NH2:1])[N:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
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%.
Workup
- temperatureto cool to room temperature
- customThe reaction mixture was put on a rotary evaporator
- customthe solvent was evaporated to the half of its original volume
- customA precipitate was formed by addition of diethyl ether (200 mL)
- filtrationThe precipitate was collected by vacuum filtration
Sources & evidence
- ORD record
- ord-0cfa03043b164fa289f5ed40aae8c9e6
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101622B2
Reaction notes
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