Sodium Hydroxide → Mepanipyrim

HRID 2166248Notes

Reaction equation

HRID 2166248 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-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C(C)=CC=CC=1>[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 2

HCID 14798Sodium HydroxideHCID 541734932-Anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine

Product 1

HCID 86296MepanipyrimYield 51.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 7237O-XyleneSolvent

Procedure

Into a 500 ml reaction flask equipped with a stirrer, a thermometer and a condenser, 51.9 g (0.2 mol) of 2-anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine and 400 ml of xylene were charged and dissolved. To this solution, 160 g (0.4 mol) of a 10% sodium hydroxide aqueous solution and 6.4 g (0.02 mol) of tetrabutylammonium bromide were added, and the mixture was reacted under reflux for 5 hours. The reaction mixture was cooled and subjected to liquid separation. The xylene layer was washed with water. The xylene layer was concentrated and subjected to column chromatography to obtain 22.8 g of 2-anilino-4-methyl-6-(1-propynyl)pyrimidine having a melting point of from 125° to 126° C. The yield was 51.1%.

Workup

  1. customInto a 500 ml reaction flask
  2. customequipped with a stirrer
  3. dissolutiondissolved
  4. customthe mixture was reacted
  5. temperatureunder reflux for 5 hours
  6. temperatureThe reaction mixture was cooled
  7. customsubjected to liquid separation
  8. washThe xylene layer was washed with water
  9. concentrationThe xylene layer was concentrated

Sources & evidence

ORD record
ord-fb43d7742812484baebeb9eed814302a
Source dataset
uspto-grants-1990_07
Patent number
US04943675

Reaction notes

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