Water → 4-Iodo-2-(methylthio)pyrimidine

HRID 659956Notes

Reaction equation

HRID 659956 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.O.C(=O)(O)[O-].[Na+].[IH:16]>>[I:16][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 24841Hydrogen iodideHCID 971134-Chloro-2-methylthiopyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 38589014-Iodo-2-(methylthio)pyrimidine

Procedure

50 g (0.31 mole) of 4-chloro-2-methylthiopyrimidine is solubilised in 300 mL of hydriodic acid at room temperature. The reaction mixture is stirred at room temperature for 8 hours. The reaction mixture is poured into 1.2 L of water and the pH adjusted to 8 with solid sodium bicarbonate. The mixture is extracted with dichloromethane and washed with sodium thiosulfate. After concentration the oily residue gives 74 g of 4-iodo-2-methylthiopyrimidine.

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. washwashed with sodium thiosulfate
  3. concentrationAfter concentration the oily residue

Sources & evidence

ORD record
ord-b1bb03958c5e4d05890d7d9f4dc26fdf
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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