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

HRID 2166252Notes

Reaction equation

HRID 2166252 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH:15]=[C:16](Cl)[CH3:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C>[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]#[C:16][CH3:17])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 541734932-Anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine

Product 1

HCID 86296MepanipyrimYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 50 ml round bottom flask, 0.52 g (0.02 mol) of 2-anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine, 4.0 g of KF/alumina and 20 ml of anhydrous acetonitrile were charged, and the mixture was stirred at room temperature for 5 hours in the flask equipped with a calcium chloride tube. Then, the mixture was subjected to filtration to remove the solid content, and the solvent was distilled off. The residue was dissolved in toluene and washed with water. This toluene layer was washed with water and concentrated, and then it was subjected to column chromatography to obtain 0.3 g of 2-anilino-4-methyl-6(1-propynyl)pyrimidine having a melting point of from 125° to 126° C. The yield was 67%.

Workup

  1. customequipped with a calcium chloride tube
  2. filtrationThen, the mixture was subjected to filtration
  3. customto remove the solid content
  4. distillationthe solvent was distilled off
  5. dissolutionThe residue was dissolved in toluene
  6. washwashed with water
  7. washThis toluene layer was washed with water
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-96b2a8dfaad24341bdcdc10765936589
Source dataset
uspto-grants-1990_07
Patent number
US04943675

Reaction notes

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