Phosphorus oxychloride → 4-Chloro-2,5-dimethyl-6-(2,4,6-trimethyl-benzyl)pyrimidine

HRID 1760700Notes

Reaction equation

HRID 1760700 reaction equation
O[C:2]1[C:7]([CH3:8])=[C:6]([CH2:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[N:5]=[C:4]([CH3:19])[N:3]=1.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:2]1[C:7]([CH3:8])=[C:6]([CH2:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[N:5]=[C:4]([CH3:19])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1784248682,5-dimethyl-6-[(2,4,6-trimethylphenyl)methyl]-1H-pyrimidin-4-one

Product 1

HCID 219124244-Chloro-2,5-dimethyl-6-(2,4,6-trimethyl-benzyl)pyrimidineYield 97%

Procedure

A mixture of 4-hydroxy-2,5-dimethyl(2,4,6-trimethyl-benzyl)-pyrimidine (1.2 g. 4.68 mmol) and POCl3 (25 ml) was heated at reflux for 1 hour. The mixture was cooled and evaporated to dryness. The residue was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to dryness to give 1.24 g (97%) of golden crystals, mp 824° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe mixture was cooled
  4. customevaporated to dryness
  5. additionThe residue was poured into ice-water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. customdried
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-45c2f1a01bba4e1a914d2869f3040ac7
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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