Phosphorus oxychloride → Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

HRID 390038Notes

Reaction equation

HRID 390038 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([S:14][CH3:15])[NH:5][C:6](=O)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:6]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:2]([CH3:1])[N:3]=[C:4]([S:14][CH3:15])[N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135504073Ethyl 4-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate

Product 1

HCID 22225416Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylateYield 87%

Procedure

A round bottom flask was charged with ethyl 4-methyl-2-(methylthio)-6-oxo-1,6-dihydro-5-pyrimidinecarboxylate (6 g) and phosphorus oxychloride (30 mL) and heated to reflux for 3 h. The phosphorus oxychloride was removed under vacuum. The residue was chromatographed (silica gel, eluting with methylene chloride) to afford the product (5.73 g, 87% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. customThe phosphorus oxychloride was removed under vacuum
  4. customThe residue was chromatographed
  5. wash(silica gel, eluting with methylene chloride)

Sources & evidence

ORD record
ord-97613ac956454d14b71035b1e1d96c1e
Source dataset
uspto-grants-2013_02
Patent number
US08383635B2

Reaction notes

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