Hydrogen iodide → 4-Iodo-2-(methylthio)pyrimidine

HRID 1159872Notes

Reaction equation

HRID 1159872 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[IH:10]>CCCCCC>[I:10][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 971134-Chloro-2-methylthiopyrimidine

Product 1

HCID 38589014-Iodo-2-(methylthio)pyrimidineYield 92%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

4-Chloro-2-methylthiopyrimidine (40 g, 249 mmol) is added to Hydroiodic acid (57% in water, 200 mL). The suspension is vigorously stirred in the absence of light for 72 h at rt. A bright yellow solid formed which is collected by filtration. The solid is added to saturated aqueous NaHCO3 (500 mL) and stirred for 2 min. CHCl3 (600 mL) is added and the solid dissolved. The aqueous layer is extracted 2 times with CHCl3 (350, then 300 mL) and the organic extracts combined, washed with water (100 mL), dried over MgSO4 and filtered. The organic solvent is removed in vacuo to give colorless oil. Addition of n-hexane and removal of solvent again produced the title compound as a white solid (57.9 g, 230 mmol, 92%).

Workup

  1. customA bright yellow solid formed which
  2. filtrationis collected by filtration
  3. additionThe solid is added to saturated aqueous NaHCO3 (500 mL)
  4. stirringstirred for 2 min
  5. additionCHCl3 (600 mL) is added
  6. dissolutionthe solid dissolved
  7. extractionThe aqueous layer is extracted 2 times with CHCl3 (350
  8. washwashed with water (100 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customThe organic solvent is removed in vacuo
  12. customto give colorless oil

Sources & evidence

ORD record
ord-9ff459b18c9c43e1aad82b252fcb7e77
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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