Phosphorus oxychloride → 2-Chloro-5-(4-fluorophenyl)-4-(4-pyridyl)-pyrimidine

HRID 398027Notes

Reaction equation

HRID 398027 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[N:10][C:11](=O)[NH:12][CH:13]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:11]1[N:10]=[C:9]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:13][N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517537HCID 178517537, compound

Product 1

HCID 230003652-Chloro-5-(4-fluorophenyl)-4-(4-pyridyl)-pyrimidine

Procedure

A mixture of 5-(4-fluorophenyl)-4-(4-pyridyl)-2-(1H)-pyrimidinone (2.41 mmol) and phosphorus oxychloride (3 ml) was heated at reflux for 45 min. It was evaporated to dryness at a bath temperature of >500° C. The flask was cooled in an ice-bath and ice-water was added. If the pH value was found still acidic, then the mixture was neutralized with aqueous 5% ammonium hydroxide. It was extracted with dichloromethane, followed by washing of the organic solution with aqueous sodium chloride, drying and evaporation to yield the title compound as a yellowish foam which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 45 min
  3. customIt was evaporated to dryness at a bath temperature of >500° C
  4. temperatureThe flask was cooled in an ice-bath
  5. additionice-water was added
  6. extractionIt was extracted with dichloromethane
  7. washby washing of the organic solution with aqueous sodium chloride
  8. customdrying
  9. customevaporation

Sources & evidence

ORD record
ord-a2c8b7eadaf44aa1b0e5754b67a0e435
Source dataset
uspto-grants-2003_08
Patent number
US06610698B2

Reaction notes

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