Hydrazine hydrate (1:1) → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(2-aminoethyl)thiomethylpyrimidine

HRID 364271Notes

Reaction equation

HRID 364271 reaction equation
[F:1][C:2]([F:30])([F:29])[CH2:3][N:4]=[C:5]([NH2:28])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][CH2:15][CH2:16][N:17]2C(=O)C3=CC=CC=C3C2=O)[N:8]=1.O.NN>C(O)C>[F:30][C:2]([F:1])([F:29])[CH2:3][N:4]=[C:5]([NH2:28])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][CH2:15][CH2:16][NH2:17])[N:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 212987504-[2-(2,2,2-Trifluoroethyl)-guanidino]-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine

Product 1

HCID 212987204-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(2-aminoethyl)thiomethylpyrimidineYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine (5.4 g.), ethanol (30 ml.) and 99% hydrazine hydrate (3 ml.) was heated under reflux for 1 hour and then evaporated to dryness. The residue was stirred with N hydrochloric acid and then filtered and the filtrate basified with 17N NaOH. The mixture was extracted with ether, and the ether extracts dried and evaporated to dryness to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[(2-aminoethyl)thiomethyl]pyrimidine (2.93 g.) which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customevaporated to dryness
  4. filtrationfiltered
  5. extractionThe mixture was extracted with ether
  6. dry with materialthe ether extracts dried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d20d300336e14edb87785bac78172f9f
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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