Sodium hydride → 2-[2-(2,2,2-Trifluoroethyl)guanidino]-6-(3-aminopropylthio)pyrazine

HRID 34823

Reaction equation

HRID 34823 reaction equation
[H-].[Na+].Cl.[NH2:4][CH2:5][CH2:6][CH2:7][SH:8].[F:9][C:10]([F:24])([F:23])[CH2:11][N:12]=[C:13]([NH2:22])[NH:14][C:15]1[CH:20]=[N:19][CH:18]=[C:17](Cl)[N:16]=1>C(O)C>[F:24][C:10]([F:9])([F:23])[CH2:11][N:12]=[C:13]([NH2:22])[NH:14][C:15]1[CH:20]=[N:19][CH:18]=[C:17]([S:8][CH2:7][CH2:6][CH2:5][NH2:4])[N:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 197870(3-Mercaptopropyl)ammonium chlorideHCID 212987082-(2,2,2-Trifluoroethyl)guanidino-6-chloropyrazine

Product 1

HCID 212988192-[2-(2,2,2-Trifluoroethyl)guanidino]-6-(3-aminopropylthio)pyrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydride (50% w/w dispersion in oil; 0.57 g.) was added to ethanol (10 ml.) portionwise. To the resulting solution was added 3-aminopropanethiol hydrochloride (0.75 g.) and the mixture stirred at room temperature. 2-[2-(2,2,2-Trifluoroethyl)guanidino]6-chloropyrazine (0.5 g.) was added in one portion and the mixture heated under reflux on the steam bath overnight. The mixture was cooled, evaporated, water (10 ml.) added and the mixture extracted with ethyl acetate. The extracts were dried over magnesium sulphate, filtered and evaporated to yield an oil, which was chromatographed eluting with methanol/methylene chloride/ammonia 10:40:1 v/v/v to yield 2-[2-(2,2,2-trifluoroethyl)guanidino]-6-(3-aminopropylthio)pyrazine as a pale yellow solid (0.39 g.) which was used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux on the steam bath overnight
  3. temperatureThe mixture was cooled
  4. customevaporated
  5. additionwater (10 ml.) added
  6. extractionthe mixture extracted with ethyl acetate
  7. dry with materialThe extracts were dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customto yield an oil, which
  11. customwas chromatographed
  12. washeluting with methanol/methylene chloride/ammonia 10:40:1 v/v/v

Sources & evidence

ORD record
ord-285923afd9e14b9ba175bba83e6df24c
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Linked notes

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