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

HRID 1902302Notes

Reaction equation

HRID 1902302 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 17 N 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-4b6425fb03ff4abfbb47140fb23d112a
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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