Phosphorus oxychloride → 2-Butylsulfanyl-4-chloro-pyrimidine

HRID 1946982

Reaction equation

HRID 1946982 reaction equation
[CH2:1]([S:5][C:6]1[NH:11][C:10](=O)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:15])=O>>[CH2:1]([S:5][C:6]1[N:11]=[C:10]([Cl:15])[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 5342184(1H)-Pyrimidinone, 2-(butylthio)-

Product 1

HCID 597434972-Butylsulfanyl-4-chloro-pyrimidine

Procedure

A mixture of 2-butylsulfanyl-3H-pyrimidin-4-one (3.0 g) and phosphorus oxychloride (15 mL) was heated at reflux for 3 h; it was then cooled to RT and evaporated under reduced pressure. The residue was poured into an ice-water mixture, and the resulting mixture was extracted with DCM. The combined organic extracts were washed with a diluted aqueous solution of NaHCO3, dried over Na2SO4, filtered and evaporated under reduced pressure to give 1.2 g of 2-butylsulfanyl-4-chloro-pyrimidine.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customevaporated under reduced pressure
  4. additionThe residue was poured into an ice-water mixture
  5. extractionthe resulting mixture was extracted with DCM
  6. washThe combined organic extracts were washed with a diluted aqueous solution of NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ee565527e61f4d31a2964b6a4274a32c
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Linked notes

Loading…