Toluene → 2-(4-Fluorophenyl)-5-propylpyrimidine

HRID 1380221Notes

Reaction equation

HRID 1380221 reaction equation
Cl.[F:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.[C:12]1([CH3:18])[CH:17]=C[CH:15]=[CH:14][CH:13]=1>CO>[CH2:13]([C:12]1[CH:17]=[N:8][C:7]([C:6]2[CH:10]=[CH:11][C:3]([F:2])=[CH:4][CH:5]=2)=[N:9][CH:18]=1)[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 1140TolueneHCID 124561604-Fluorobenzamidine Hydrochloride

Product 1

HCID 7756512-(4-Fluorophenyl)-5-propylpyrimidineYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a sodium methylate solution under agitation obtained by dissolving Na (2.8 g, 0.12 mol) in anhydrous methanol (20 c.c.) was added 4-fluorobenzamidine hydrochloride (10.5 g, 0.06 mol), followed by adding α-propyl-β-dimethylaminoacrolein (9.2 g, 0.06 mol), thereafter refluxing on heating for 3 hours with stirring, distilling off methanol under the atmospheric pressure after completion of the reaction, adding toluene (20cc) to the reaction residue to extract the resulting product, washing the extraction liquid with water, drying with anhydrous sodium sulfate, distilling off toluene and recrystallizing the remaining oily substance from ethanol (20 c.c.) to obtain the objective 5-propyl-2-(4-fluorophenyl)pyrimidine (7.0 g). Yield: 55%. M.P. 52.7° C.

Workup

  1. temperaturerefluxing
  2. temperatureon heating for 3 hours
  3. distillationdistilling off methanol under the atmospheric pressure
  4. customafter completion of the reaction
  5. extractionto extract the resulting product
  6. washwashing
  7. extractionthe extraction liquid with water
  8. dry with materialdrying with anhydrous sodium sulfate
  9. distillationdistilling off toluene
  10. customrecrystallizing the remaining oily substance from ethanol (20 c.c.)

Sources & evidence

ORD record
ord-2bf9ab1d0524445cbfb8f6716166494a
Source dataset
uspto-grants-1986_04
Patent number
US04581155

Reaction notes

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