Toluene → Mepanipyrim

HRID 2166249Notes

Reaction equation

HRID 2166249 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.[OH-].[K+].C1(C)C=CC=CC=1>O>[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

5

Reactant 3

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 541734932-Anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine

Product 1

HCID 86296MepanipyrimYield 37.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 100 ml reaction flask equipped with a stirrer, a thermometer and a condenser, 5.2 g (0.02 mol) of 2-anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine, 1.3 g (0.024 mol) of finely pulverized KOH and 50 ml of toluene were charged, and the mixture was reacted for 10 hours under reflux. The reaction mixture was cooled, water was added, and the mixture was subjected to liquid separation. The toluene layer was washed with water. The toluene layer was concentrated and subjected to column chromatography to obtain 1.67 g of 2-anilino-4-methyl-6-(1-propynyl)pyrimidine having a melting point of from 125° to 126° C. The yield was 37.4%.

Workup

  1. customInto a 100 ml reaction flask
  2. customequipped with a stirrer
  3. customthe mixture was reacted for 10 hours
  4. temperatureunder reflux
  5. temperatureThe reaction mixture was cooled
  6. customthe mixture was subjected to liquid separation
  7. washThe toluene layer was washed with water
  8. concentrationThe toluene layer was concentrated

Sources & evidence

ORD record
ord-9aaeb2b573de46dfa7ef16ad28598345
Source dataset
uspto-grants-1990_07
Patent number
US04943675

Reaction notes

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