Hydrogen iodide → HCID 90014635, compound

HRID 626885Notes

Reaction equation

HRID 626885 reaction equation
[IH:1].Cl[C:3]1[N:8]=[C:7]([CH3:9])[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:4]=1>C(Cl)Cl>[I:1][C:3]1[N:8]=[C:7]([CH3:9])[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:4]=1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 574686142-Chloro-4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidine

Product 1

HCID 90014635HCID 90014635, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydroiodic acid (57% in water, 9.68 mL, 73.41 mmol) was added portionwise to 2-chloro-4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine (which may be prepared as described in Description 11) (1.38 g, 5.06 mmol) in DCM (30 mL) at 20° C. and the dark mixture was stirred for 18 hrs. The mixture was quenched by the addition of sat. aq. K2CO3 (care: gas evolved). After basification, satd. aq. sodium metabisulphite was added and stirring was continued for 5 mins. The mixture was diluted with further DCM and the phases were separated. The organic layer was dried (Na2SO4) and the solvent evaporated to afford 2-iodo-4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine (D12) (1.58 g, 4.34 mmol, 85.7% yield) a yellow solid, containing about 20% of the reduced H-compound.

Workup

  1. customThe mixture was quenched by the addition of sat. aq. K2CO3 (care: gas evolved)
  2. additionaq. sodium metabisulphite was added
  3. stirringstirring
  4. waitwas continued for 5 mins
  5. additionThe mixture was diluted with further DCM
  6. customthe phases were separated
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-ae0078101b7e4cf59f239ea49d0a01d6
Source dataset
uspto-grants-2016_04
Patent number
US09309254B2

Reaction notes

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