Ammonia → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine
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]=1Participants
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 1N hydrochloric acid and then filtered and the filtrate basified with 17N 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
- filtrationfiltered
- customthe filtrate evaporated to dryness
- additionA solution of the residue in ethanol (10 ml.) was treated with hydrazine hydrate (1 ml.)
- temperaturethe mixture heated
- temperatureunder reflux for 1 hour
- customevaporated to dryness
- stirringThe residue was stirred with 1N hydrochloric acid
- filtrationfiltered
- extractionThe mixture was extracted with ether
- dry with materialthe combined ether extracts dried
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-18d9153dd9ca4dda9fa425e08d3cab46
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04762932
Reaction notes
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