Hydrochloric Acid → 4-Chloro-6-ethyl-5-fluoropyrimidine

HRID 2384510Notes

Reaction equation

HRID 2384510 reaction equation
C(N(CC)CC)C.[CH2:8]([C:10]1[N:15]=[CH:14][N:13]=[C:12](O)[C:11]=1[F:17])[CH3:9].[ClH:18]>ClCCl.P(Cl)(Cl)(Cl)=O>[Cl:18][C:12]1[C:11]([F:17])=[C:10]([CH2:8][CH3:9])[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 178437743HCID 178437743, compound

Product 1

HCID 167434454-Chloro-6-ethyl-5-fluoropyrimidineYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

78.24 ml of triethylamine was added to a solution prepared by dissolving 80 g of 6-ethyl-5-fluoro-4-hydroxypyrimidine in 240 ml of dichloromethane, and 57.4 ml of phosphorus oxychloride was slowly added thereto over 30 min. The resulting solution was refluxed for 5 hours to complete the reaction, and cooled to room temperature. Then, 352 ml of 3N HCl was added thereto while maintaining the temperature at below 20° C. The resulting aqueous mixture was extracted with 100 ml of dichloromethane. The organic layer was washed with 100 ml of water, was dried over magnesium sulfate, and concentrated under a reduced pressure to obtain the title compound as an oil (85.9 g, yield: 95%).

Workup

  1. customprepared
  2. additionwas slowly added
  3. temperatureThe resulting solution was refluxed for 5 hours
  4. customthe reaction
  5. temperaturewhile maintaining the temperature at below 20° C
  6. extractionThe resulting aqueous mixture was extracted with 100 ml of dichloromethane
  7. washThe organic layer was washed with 100 ml of water
  8. dry with materialwas dried over magnesium sulfate
  9. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-c2751b0611aa4323987a6550b8e31236
Source dataset
uspto-grants-2012_09
Patent number
US08263769B2

Reaction notes

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