N-Iodosuccinimide → 5-Iodo-6-methylpyrimidin-4-ol
Reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4][N:3]=1.C1C(=O)N([I:16])C(=O)C1>C(O)(=O)C>[I:16][C:7]1[C:2](=[O:1])[NH:3][CH:4]=[N:5][C:6]=1[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stiffed solution of 70 g (0.64 mol) 4-hydroxy-6-methyl pyrimidine in acetic acid is added 127 g (0.56 mol) NIS portion wise at RT within 15 min The reaction is stiffed for to 30 h at RT until all starting material is consumed. The reaction mixture is diluted with water and the solid product is filtered off and washed with sodium thiosulfate solution to remove excess iodine. After drying, the desired product is obtained as a pale brown solid (90 g; 60%) which is used without further purification.
Workup
- customis stiffed for to 30 h at RT until all starting material
- customis consumed
- additionThe reaction mixture is diluted with water
- filtrationthe solid product is filtered off
- washwashed with sodium thiosulfate solution
- customto remove excess iodine
- customAfter drying
Sources & evidence
- ORD record
- ord-2165674d323d4c579f31d0dfb587961d
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618111B2
Reaction notes
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