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3-Amino-1-propanol → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropyloxy)pyrimidine

HRID 34791
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 34791
[F:1][C:2]([F:19])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9](S(C)(=O)=O)[N:8]=1.[NH2:20][CH2:21][CH2:22][CH2:23][OH:24].[H-].[Na+]>C(O)(C)(C)C>[F:1][C:2]([F:19])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:24][CH2:23][CH2:22][CH2:21][NH2:20])[N:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 90863-Amino-1-propanolHCID 24758Sodium hydrideHCID 212797704-[2-(2,2,2-Trifluoroethyl)guanidino]-2-methylsulphonylpyrimidine

Produkt 1

HCID 212988144-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropyloxy)pyrimidineAusbeute 47,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-methylsulphonylpyrimidine (0.15 g.) was added to a mixture of 3-aminopropanol (0.075 g.), t-butanol (5 ml.) and a 50% w/w dispersion of sodium hydride in mineral oil (0.05 g.) which was stirred under an argon atmosphere. The mixture was stirred at room temperature for 2 hours, heated under reflux for 4 hours and then evaporated to dryness. The residue was partitioned between 2N aqueous acetic acid and ether, and the aqueous phase basified with 17N NaOH and extracted three times with ether. The combined ether extracts were dried and evaporated to dryness to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(3-aminopropyloxy)pyrimidine (0.07 g.) which was used without further purification.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customevaporated to dryness
  4. customThe residue was partitioned between 2N aqueous acetic acid and ether
  5. extractionextracted three times with ether
  6. dry with materialThe combined ether extracts were dried
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-31ecbbacedb24809b4177087bbf70ce6
Quelldatensatz
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04762932

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