Phosphorus oxychloride → 4-Chloro-6-methyl-2-(methylthio)pyrimidine

HRID 617785Notes

Reaction equation

HRID 617785 reaction equation
O[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178503447HCID 178503447, compound

Product 1

HCID 2411634-Chloro-6-methyl-2-(methylthio)pyrimidineYield 80%

Procedure

4-Hydroxy-6-methyl-2-(methylthio)pyrimidine (9.20 g, 59 mmol) and phosphorous oxychloride (60 mL) were combined and refluxed for 3 hours. The reaction mixture was cooled to room temperature and poured onto crushed ice. The resultant aqueous mixture was extracted with ethyl acetate; and the organic layer washed with saturated aqueous sodium bicarbonate followed by a water wash, dried over magnesium sulfate, and dried in vacuo to give 4-chloro-6-methyl-2-(methylthio)pyrimidine (8.27 g, 80%), m.p. 37-38° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. additionpoured
  3. customonto crushed ice
  4. extractionThe resultant aqueous mixture was extracted with ethyl acetate
  5. washand the organic layer washed with saturated aqueous sodium bicarbonate
  6. washwash
  7. dry with materialdried over magnesium sulfate
  8. customdried in vacuo

Sources & evidence

ORD record
ord-cd5551f7f35444d0abf193a41b49fc09
Source dataset
uspto-grants-1999_09
Patent number
US05952331

Reaction notes

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