Sodium Iodide → 4-Iodo-2-(methylthio)-5-(trifluoromethyl)pyrimidine

HRID 1473027Notes

Reaction equation

HRID 1473027 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([S:12][CH3:13])[N:3]=1.[I-:14].[Na+].I>O>[I:14][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([S:12][CH3:13])[N:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 584645664-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine

Product 1

HCID 717433934-Iodo-2-(methylthio)-5-(trifluoromethyl)pyrimidineYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine (I13) (5.00 g, 21.9 mmol) was placed into a reaction flask then sodium iodide (9.80 g, 65.6 mmol) and hydroiodic acid (58%; 70 mL) were added. The reaction mixture was stirred for 48 hours in darkness then diluted with water (200 mL) where upon a colourless solid precipitated. The precipitate was collected by filtration and was washed with 10% NaHCO3 solution until neutral. The resulting solid was washed with water (100 mL) then suction dried for 2 hours to give the title compound (I14) (3.956 g, 57%) as a pale yellow solid; 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 2.58 (s, 3H). LCMS Method C: rt 6.30 min, m/z 321.0 [M+H]+.

Workup

  1. customprecipitated
  2. filtrationThe precipitate was collected by filtration
  3. washwas washed with 10% NaHCO3 solution until neutral
  4. washThe resulting solid was washed with water (100 mL)
  5. customsuction dried for 2 hours

Sources & evidence

ORD record
ord-f7c84e3fd8ff4df8919e6f545c62018f
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

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