Phosphorus oxychloride → 2-Chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine

HRID 4325

Reaction equation

HRID 4325 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:16][C:15](=O)[N:14]([CH3:18])[C:13](=[N:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Cl)(Cl)([Cl:31])=O>>[Cl:31][C:15]1[N:14]([CH3:18])[C:13](=[N:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[CH:12]=[C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:16]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178418505HCID 178418505, compound

Product 1

HCID 201522932-Chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine

Procedure

To 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)-2-(1H)pyrimidone (5.0 g) was added phosphorus oxychloride (50 ml). The mixture was refluxed for 7 hours and evaporated under reduced pressure. The resulting syrup was triturated in a mixture of ice and water, neutralized with aqueous sodium bicarbonate and extracted with chloroform. The extract was dried and evaporated under reduced pressure. The residue was chromatographed on silica gel using chloroform to give 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (3.26 g).

Workup

  1. temperatureThe mixture was refluxed for 7 hours
  2. customevaporated under reduced pressure
  3. customThe resulting syrup was triturated in a mixture of ice and water
  4. extractionextracted with chloroform
  5. customThe extract was dried
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-53723e478eea4102a066bd715aecef75
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Linked notes

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