Phosphorus oxychloride → HCID 75132210, compound

HRID 733165Notes

Reaction equation

HRID 733165 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7](O)[CH:6]=[C:5]([CH2:10][CH2:11][CH3:12])[N:4]=1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:7]1[CH:6]=[C:5]([CH2:10][CH2:11][CH3:12])[N:4]=[C:3]([S:2][CH3:1])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178439474HCID 178439474, compound

Product 1

HCID 75132210HCID 75132210, compoundYield 100%

Procedure

A suspension of 2-methylsulfanyl-6-propyl-pyrimidin-4-ol (15.5 g) in phosphorous oxychloride (160 mL) was refluxed for 6 hours. The solvent was distilled off under reduced pressure. The residue was diluted with dichloromethane and poured in ice. The layers were separated, then the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulphate, filtered and concentrated under reduced pressure to afford 4-chloro-2-methylsulfanyl-6-propyl-pyrimidine (17.5 g, 100%) as an orange oil.

Workup

  1. temperaturewas refluxed for 6 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionThe residue was diluted with dichloromethane
  4. additionpoured in ice
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted twice with ethyl acetate
  7. dry with materialThe combined organic layers were dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dbc8083594df4f29ad763c49b9874c4d
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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