Ammonia → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine

HRID 1902266Notes

Reaction equation

HRID 1902266 reaction equation
[F:1][C:2]([F:30])([F:29])[CH2:3][NH:4][C:5](=S)[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3=CC=CC=C3C2=O)[N:8]=1.[NH3:31]>CN(C=O)C>[F:30][C:2]([F:1])([F:29])[CH2:3][N:4]=[C:5]([NH2:31])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][NH2:17])[N:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 867386674-[3-(2,2,2-Trifluoroethyl)thioureido]-[(3-phthalimido)propylthio]pyrimidine

Product 1

HCID 212987114-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[3-(2,2,2-trifluoroethyl)thioureido]-[(3-phthalimido)propylthio]pyrimidine (0.4 g.), N,N,-dimethylformamide (5 ml.), saturated ethanolic ammonia (10 ml.) and yellow mercuric oxide (280 mg.) was stirred at room temperature for 3 hours and then filtered and the filtrate evaporated to dryness. A solution of the residue in ethanol (10 ml.) was treated with hydrazine hydrate (1 ml.), the mixture heated under reflux for 1 hour and then evaporated to dryness. The residue was stirred with 1 N hydrochloric acid and then filtered and the filtrate basified with 17 N NaOH. The mixture was extracted with ether and the combined ether extracts dried and evaporated to dryness to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[(3-amino)propylthio]-pyrimidine which was used without further purification.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness
  3. additionA solution of the residue in ethanol (10 ml.) was treated with hydrazine hydrate (1 ml.)
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 1 hour
  6. customevaporated to dryness
  7. stirringThe residue was stirred with 1 N hydrochloric acid
  8. filtrationfiltered
  9. extractionThe mixture was extracted with ether
  10. dry with materialthe combined ether extracts dried
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-1c1072b8c9c74de3a2db9cfabc1ef38c
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

Loading…