N-Iodosuccinimide → HCID 117677754, compound

HRID 1507476Notes

Reaction equation

HRID 1507476 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([S:10][CH3:11])[N:3]=1.C1C(=O)N([I:19])C(=O)C1>CC#N>[Cl:1][C:2]1[C:7]([I:19])=[C:6]([O:8][CH3:9])[N:5]=[C:4]([S:10][CH3:11])[N:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 98369994-Chloro-6-methoxy-2-(methylthio)pyrimidine

Product 1

HCID 117677754HCID 117677754, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 2 (10 g, 52.5 mmol) was dissolved in MeCN (150 mL) and NIS (14.2 g, 62.9 mmol) was added. The solution was heated to reflux for 5 h and cooled to room temperature. The solvent was evaporated and the residue was dissolved in EtOAc. The organics were washed with sat. NaHCO3 and sat. NaS2O3, dried (MgSO4), filtered and concentrated to give the title compound as a white solid. 1H NMR (CDCl3) δ 4.04 (s, 3H), 2.54 (s, 3H); LCMS 2.64 min, 317 (M+H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThe organics were washed with sat. NaHCO3 and sat. NaS2O3
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-467c88c658d245f499f464b102b12d1c
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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