Sodium Carbonate → 4-Iodo-2-(methylthio)pyrimidine

HRID 888027Notes

Reaction equation

HRID 888027 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[IH:10].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>>[I:10][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 24841Hydrogen iodideHCID 971134-Chloro-2-methylthiopyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 38589014-Iodo-2-(methylthio)pyrimidineYield 69%

Procedure

4-Chloro-2-methylthiopyrimidine (5 g, 31.15 mmol) was added dropwise to a cooled 57% aqueous hydriodic acid solution (0° C.). Stirring was continued at 0° C. for 30 minutes, before warming to ambient temperature and stirring for 24 hours. Aqueous sodium bicarbonate was then carefully added and the resultant suspension basified to pH 9 by addition of sodium carbonate. The mixture was extracted with ethyl acetate and the extracts dried over magnesium sulfate and concentrated by reduced pressure. The resultant solid was dissolved in boiling isohexane and cooled by refridgeration overnight. The resultant solid was filtered and dried to afford the title compound as colourless needles (5.4 g, 69%); NMR Spectrum: (CDCl3) 2.55 (s, 3H), 7.40 (d, 1H), 7.98 (d, 1H); Mass Spectrum: M+H+ 253.

Workup

  1. stirringstirring for 24 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe extracts dried over magnesium sulfate
  4. concentrationconcentrated by reduced pressure
  5. dissolutionThe resultant solid was dissolved
  6. temperaturecooled by refridgeration overnight
  7. filtrationThe resultant solid was filtered
  8. customdried

Sources & evidence

ORD record
ord-ecbb99f811f549b18ea3f80f716e35f5
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

Loading…