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

HRID 343844Notes

Reaction equation

HRID 343844 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-98a5dd7fdda34899b5a9b85033b0fa91
Source dataset
uspto-grants-1999_01
Patent number
US05863924

Reaction notes

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