Phosphorus oxychloride → 4-Chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine

HRID 4323

Reaction equation

HRID 4323 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([CH3:17])[NH:14][C:13](=O)[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:13]1[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]=[C:15]([CH3:17])[N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1357361743,4-Dihydro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidin-4-one

Product 1

HCID 201522714-Chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine

Procedure

A suspension of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidin-4-one (2.4 g) in phosphorus oxychloride (20 ml) was refluxed for 2 hours, and evaporated. To the residue were added aqueous sodium bicarbonate solution and chloroform, and stirred at ambient temperature for 2 hours. The organic layer was obtained and washed with water. After evaporated, the residue was dissolved in ethyl acetate-diisopropyl ether mixture (1:6 v/v). The precipitates were filtered off, and the filtrate was evaporated to give 4-chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (2.09 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customevaporated
  3. additionTo the residue were added aqueous sodium bicarbonate solution and chloroform
  4. customThe organic layer was obtained
  5. washwashed with water
  6. customAfter evaporated
  7. dissolutionthe residue was dissolved in ethyl acetate-diisopropyl ether mixture (1:6 v/v)
  8. filtrationThe precipitates were filtered off
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-6d50e5f7c65748e8bdcac9917b03d8e2
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Linked notes

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