Hydrazine hydrate (1:1) → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(2-aminoethylthio)pyrimidine

HRID 34800Notes

Reaction equation

HRID 34800 reaction equation
[F:1][C:2]([F:29])([F:28])[CH2:3][N:4]=[C:5]([NH2:27])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)[N:8]=1.O.NN>C(O)C>[F:29][C:2]([F:1])([F:28])[CH2:3][N:4]=[C:5]([NH2:27])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][NH2:16])[N:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 212987304-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(2-phthalimidoethylthio)pyrimidine

Product 1

HCID 212988314-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(2-aminoethylthio)pyrimidineYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(2-phthalimidoethylthio)pyrimidine (0.6 g.) ethanol (20 ml.) and 99% hydrazine hydrate (0.5 ml.) was heated under reflux for 1 hour and then evaporated to dryness. The residue was stirred with N hydrochloric acid and the mixture filtered. The filtrate was basified with 17N NaOH and the mixture extracted three times with ether. The combined ether extracts were dried and then evaporated to dryness to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(2-aminoethylthio)pyrimidine (0.25 g.) which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customevaporated to dryness
  4. filtrationthe mixture filtered
  5. extractionthe mixture extracted three times with ether
  6. dry with materialThe combined ether extracts were dried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c73bab9fc43b49d7ad23e75a2c95f975
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Reaction notes

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