Phosphorus oxychloride → HCID 63549460, compound

HRID 2401207Notes

Reaction equation

HRID 2401207 reaction equation
[CH2:1]([C:3]1[NH:8][CH:7]=[N:6][C:5](=O)[C:4]=1[CH3:10])[CH3:2].P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:5]1[C:4]([CH3:10])=[C:3]([CH2:1][CH3:2])[N:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178437829HCID 178437829, compound2×

Product 1

HCID 63549460HCID 63549460, compoundYield 84.3%

Procedure

6-Ethyl-5-methyl-4(1H)-pyrimidinone (Intermediate 40, 1.382 g, 10 mmol) was added to a stirred solution of phosphorus oxychloride (4.66 ml, 50.0 mmol) and the reaction mixture was heated under reflux for 2 hours. After this time the reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure. The viscous residue was dissolved in DCM and the resulting residue was poured into a stirred mixture of ice and 2M aqueous hydrochloric acid and the extracted with DCM (×3). The DCM layers were combined dried suing a hydrophobic frit and evaporated under reduced pressure to give the product, 4-chloro-6-ethyl-5-methylpyrimidine (1.32 g, 8.43 mmol) as an oil. m/z (ES+) 157/159 (M+1).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe viscous residue was dissolved in DCM
  5. additionthe resulting residue was poured into a stirred mixture of ice and 2M aqueous hydrochloric acid
  6. extractionthe extracted with DCM (×3)
  7. dry with materialThe DCM layers were combined dried
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-11b818db0f7d4622bac0935ccd080bde
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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