N-Iodosuccinimide → 5-Iodo-6-methylpyrimidin-4-ol

HRID 1916162Notes

Reaction equation

HRID 1916162 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

HCID 120273N-IodosuccinimideHCID 178429389HCID 178429389, compound

Product 1

HCID 1354674485-Iodo-6-methylpyrimidin-4-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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

  1. customis stiffed for to 30 h at RT until all starting material
  2. customis consumed
  3. additionThe reaction mixture is diluted with water
  4. filtrationthe solid product is filtered off
  5. washwashed with sodium thiosulfate solution
  6. customto remove excess iodine
  7. customAfter drying

Sources & evidence

ORD record
ord-2165674d323d4c579f31d0dfb587961d
Source dataset
uspto-grants-2013_12
Patent number
US08618111B2

Reaction notes

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