Hydrogen iodide → 4-Iodo-2-methyl-6-(methylthio)pyrimidine

HRID 1621649Notes

Reaction equation

HRID 1621649 reaction equation
Cl[C:2]1[CH:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[IH:11]>C(Cl)Cl>[I:11][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 569244304-Chloro-2-methyl-6-(methylthio)pyrimidine

Product 1

HCID 772312674-Iodo-2-methyl-6-(methylthio)pyrimidineYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-chloro-2-methyl-6-(methylthio)pyrimidine (5.3 g, 30.3 mmol) and hydriodic acid (67% solution, 5.71 mL, 76 mmol, Alfea Aesar, Avocado, Lancaster) in DCM (20 mL) was stirred at room temperature for 20 h and filtered. The collected solid was washed with DCM and then suspended in saturated NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated to give 4-iodo-2-methyl-6-(methylthio)pyrimidine (7.3 g, 27.4 mmol, 90% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.43 (s, 1H); 2.62 (s, 3H); 2.52 (s, 3H). m/z (ESI, +ve ion) 266 (M+H)+.

Workup

  1. filtrationfiltered
  2. washThe collected solid was washed with DCM
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5cc371bc0fc1442d9f29a7e86ca3a1c1
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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