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

HRID 632873Notes

Reaction equation

HRID 632873 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 stirred solution of 70 g (0.64 mol) 4-hydroxy-6-methylpyrimidine 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 pale brown solid (90 g; 60%) 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-23e4b1c684014c12b2ab4cf61b45ce9d
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

Loading…