N-Iodosuccinimide → 6-Ethyl-5-iodopyrimidin-4(1H)-one

HRID 471388Notes

Reaction equation

HRID 471388 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[CH:4][N:3]=1.C1C(=O)N([I:17])C(=O)C1>C(O)(=O)C>[CH2:8]([C:6]1[N:5]=[CH:4][NH:3][C:2](=[O:1])[C:7]=1[I:17])[CH3:9]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178436949HCID 178436949, compound

Product 1

HCID 1357061486-Ethyl-5-iodopyrimidin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 70 g (0.56 mol) 4-hydroxy-6-ethyl pyrimidine in acetic acid is added 127 g (0.56 mol) NIS portion wise at RT within 15 min The reaction is stirred for 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 solid (90 g; 64%) which is used without further purification.

Workup

  1. customis consumed
  2. additionThe reaction mixture is diluted with water
  3. filtrationthe solid product is filtered off
  4. washwashed with sodium thiosulfate solution
  5. customto remove excess iodine
  6. customAfter drying

Sources & evidence

ORD record
ord-cee68817c540488886cd5df56437dc5b
Source dataset
uspto-grants-2014_01
Patent number
US08633183B2

Reaction notes

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