Acetonitrile → HCID 21298702, compound

HRID 364320Notes

Reaction equation

HRID 364320 reaction equation
[F:1][C:2]([F:10])([CH:7]([F:9])[F:8])[CH2:3][N:4]=[C:5]=S.C1(=O)[N:15]([CH2:16][CH2:17][CH2:18][S:19][C:20]2[N:25]=[C:24]([NH2:26])[CH:23]=[CH:22][N:21]=2)C(=O)C2=CC=CC=C12.C(#[N:35])C>CN(C)C=O.N>[F:1][C:2]([F:10])([CH:7]([F:9])[F:8])[CH2:3][N:4]=[C:5]([NH2:35])[NH:26][C:24]1[CH:23]=[CH:22][N:21]=[C:20]([S:19][CH2:18][CH2:17][CH2:16][NH2:15])[N:25]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 212797361,1,2,2-Tetrafluoro-3-isothiocyanatopropaneHCID 21298869HCID 21298869, compound

Product 1

HCID 21298702HCID 21298702, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6228DimethylformamideSolvent

Procedure

2,2,3,3-Tetrafluoropropylisothiocyanate (0.9 g.) and 2-(3-phthalimidopropylthio)-4-aminopyrimidine (0.9 g.) were dissolved in acetonitrile (30 ml.) and heated under reflux for 64 hours. The resulting suspension was cooled, filtered and the collected solid washed with acetonitrile (10 ml.) to give a white solid (0.9 g.). This was dissolved in a mixture of dimethylformamide (10 ml.) and saturated ethanolic ammonia solution (5 ml.) and treated with yellow mercuric oxide (0.8 g.). The mixture was stirred at room temperature for 3 hours. The solvent was evaporated and the black residue was triturated with ethyl acetate and filtered. The solvent was evaporated and the residual gum was dissolved in ethanol (15 ml.) and added to a solution of hydrazine (5 ml.) in ethanol (10 ml.). The mixture was stirred at room temperature for 2 hours then the solvent was evaporated. The residue was triturated with 1N hydrochloric acid, filtered and the filtrate was basified with 10N sodium hydroxide solution. The product was extracted with ethyl acetate, dried (magnesium sulphate) and the solvent was evaporated to give 4-[2-(2,2,3,3-tetrafluoropropyl)guanidino]-2-[3-aminopropylthio]pyrimidine (0.5 g.) which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 64 hours
  3. temperatureThe resulting suspension was cooled
  4. filtrationfiltered
  5. washthe collected solid washed with acetonitrile (10 ml.)
  6. customto give a white solid (0.9 g.)
  7. customThe solvent was evaporated
  8. customthe black residue was triturated with ethyl acetate
  9. filtrationfiltered
  10. customThe solvent was evaporated
  11. dissolutionthe residual gum was dissolved in ethanol (15 ml.)
  12. additionadded to a solution of hydrazine (5 ml.) in ethanol (10 ml.)
  13. stirringThe mixture was stirred at room temperature for 2 hours
  14. customthe solvent was evaporated
  15. customThe residue was triturated with 1N hydrochloric acid
  16. filtrationfiltered
  17. extractionThe product was extracted with ethyl acetate
  18. dry with materialdried (magnesium sulphate)
  19. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e898f1fb6b5642c5bf8126cbfb326ea3
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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