Hydrogen iodide → 4-(5-Ethoxy-2-fluoro-phenyl)-2-iodo-6-methyl-pyrimidine

HRID 626898Notes

Reaction equation

HRID 626898 reaction equation
[IH:1].Cl[C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[C:13]([O:15][CH2:16][CH3:17])[CH:12]=[CH:11][C:10]=2[F:18])[CH:6]=[C:5]([CH3:19])[N:4]=1>C(Cl)Cl>[CH2:16]([O:15][C:13]1[CH:12]=[CH:11][C:10]([F:18])=[C:9]([C:7]2[CH:6]=[C:5]([CH3:19])[N:4]=[C:3]([I:1])[N:8]=2)[CH:14]=1)[CH3:17]

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 900153922-Chloro-4-(5-ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidine

Product 1

HCID 900151884-(5-Ethoxy-2-fluoro-phenyl)-2-iodo-6-methyl-pyrimidineYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydroiodic acid (57% in water, 8 mL, 106.39 mmol) was added portionwise to 2-chloro-4-(5-ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidine (which may be prepared as described in Description 16) (2.18 g, 8.17 mmol) in DCM (30 mL) at 20° C. and the dark mixture was stirred for 18 hrs. The mixture was filtered and washed with a little DCM. The yellow solid was suspended in water/DCM and quenched by the addition of satd. 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 4-(5-ethoxy-2-fluoro-phenyl)-2-iodo-6-methyl-pyrimidine (D17) (1.68 g, 4.6908 mmol, 57.4% yield) as a colourless oil.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with a little DCM
  3. customquenched by the addition of satd
  4. additionaq. sodium metabisulphite was added
  5. stirringstirring
  6. waitwas continued for 5 mins
  7. additionThe mixture was diluted with further DCM
  8. customthe phases were separated
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-e37868611b9f4ba982028ef3de2cc066
Source dataset
uspto-grants-2016_04
Patent number
US09309254B2

Reaction notes

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