Phosphorus oxychloride → 4-Chloro-6-methyl-5-(2-propyl)-2-(trifluoromethyl)pyrimidine

HRID 1742024Notes

Reaction equation

HRID 1742024 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[NH:5][C:4](=O)[C:3]=1[CH:13]([CH3:15])[CH3:14].O(C)[Na].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:4]1[C:3]([CH:13]([CH3:15])[CH3:14])=[C:2]([CH3:1])[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 136043553HCID 136043553, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 541318744-Chloro-6-methyl-5-(2-propyl)-2-(trifluoromethyl)pyrimidineYield 58%

Procedure

6-Methyl-5-(2-propyl)-2-trifluoromethyl-4H-pyrimidin-4-one of Example 3 (1.66 g, 7.5 mmol) was converted to a Na salt with NaOCH3 then refluxed with phosphorus oxychloride (6 mL) for 3 h. The reaction mixture was concentrated to a small volume, poured into crushed ice, and extracted with Et2O. The organic layer was washed with H2O (twice), dried over Na2SO4, and evaporated to give 1.05 g (58%) of a light yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated to a small volume
  2. additionpoured
  3. custominto crushed ice
  4. extractionextracted with Et2O
  5. washThe organic layer was washed with H2O (twice),
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-482a29f2117f41d7b67368a023e4e754
Source dataset
uspto-grants-1994_08
Patent number
US05336677

Reaction notes

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