Phosphorus oxychloride → 4-Chloro-6-ethyl-5-fluoropyrimidine

HRID 964952Notes

Reaction equation

HRID 964952 reaction equation
[CH2:1]([C:3]1[N:8]=[CH:7][NH:6][C:5](=O)[C:4]=1[F:10])[CH3:2].P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:5]1[C:4]([F:10])=[C:3]([CH2:1][CH3:2])[N:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354053876-ethyl-5-fluoro-4(3H)-pyrimidone

Product 1

HCID 167434454-Chloro-6-ethyl-5-fluoropyrimidineYield 66%

Procedure

A mixture of the product of part (i) (6.4 g, 45 mmol) and phosphoryl chloride (30 ml) was heated under reflux for 3 hours. The excess phosphoryl chloride was removed by distillation under reduced pressure and the residue was poured into ice-water. The resulting mixture was extracted with methylene chloride (3×50 ml) and the combined organic extracts were washed with water and dried over magnesium sulphate. The solvent was removed under reduced pressure and the resulting oil was distilled under reduced pressure to provide the title compound (4.81 g, 66%), b.p. 74° C. at 22 mm Hg, which was characterised by 1H-NMR spectroscopy.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe excess phosphoryl chloride was removed by distillation under reduced pressure
  4. additionthe residue was poured into ice-water
  5. extractionThe resulting mixture was extracted with methylene chloride (3×50 ml)
  6. washthe combined organic extracts were washed with water
  7. dry with materialdried over magnesium sulphate
  8. customThe solvent was removed under reduced pressure
  9. distillationthe resulting oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-950d8dc92edc4cc083aeefe14075247e
Source dataset
uspto-grants-1998_06
Patent number
US05773443

Reaction notes

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