Toluene → 2-Anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine

HRID 2166247Notes

Reaction equation

HRID 2166247 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH2:15][C:16]([CH3:18])=O)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.P(Cl)(Cl)([Cl:28])=O>O.C1(C)C=CC=CC=1>[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH:15]=[C:16]([Cl:28])[CH3:18])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 146741421-(6-Methyl-2-(phenylamino)pyrimidin-4-yl)propan-2-one

Product 1

HCID 541734932-Anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidineYield 94.4%

Reagents, catalysts & solvents 1

HCID 22272177Toluene waterSolvent

Procedure

Into a 500 ml reaction flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel, 48.3 g (0.2 mol) of 2-anilino-4-methyl-6-acetonyl-pyrimidine and 200 ml of toluene were charged and dissolved. To this solution, 61.4 g (0.4 mol) of phosphorus oxychloride was dropwise added from the dropping funnel. The mixture was reacted at a temperature of from 88° to 90° C. for further 6 hours. The reaction mixture was cooled and put into a water/toluene solution and subjected to liquid separation. The toluene layer was washed with an aqueous sodium carbonate solution and then with water. The toluene layer was concentrated to obtain 49 g of 2-anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine having a melting point of from 63° to 66° C. The yield was 94.4%.

Workup

  1. customInto a 500 ml reaction flask
  2. customequipped with a stirrer
  3. dissolutiondissolved
  4. customThe mixture was reacted at a temperature of from 88° to 90° C. for further 6 hours
  5. temperatureThe reaction mixture was cooled
  6. customsubjected to liquid separation
  7. washThe toluene layer was washed with an aqueous sodium carbonate solution
  8. concentrationThe toluene layer was concentrated

Sources & evidence

ORD record
ord-349ccdb307714f8ab4f9369e68485a79
Source dataset
uspto-grants-1990_07
Patent number
US04943675

Reaction notes

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