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Chloroacetonitrile → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[5-cyanomethylaminopentyl]pyrimidine

HRID 1462346
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1462346
[F:1][C:2]([F:21])([F:20])[CH2:3][N:4]=[C:5]([NH2:19])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[N:8]=1.Cl[CH2:23][C:24]#[N:25].C(N(CC)CC)C>CCO>[F:21][C:2]([F:1])([F:20])[CH2:3][N:4]=[C:5]([NH2:19])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:23][C:24]#[N:25])[N:8]=1
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Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 202086774-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(5-aminopentyl)pyrimidine

Produkt 1

HCID 202469524-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[5-cyanomethylaminopentyl]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(5-aminopentyl)pyrimidine (0.61 g.), chloroacetonitrile (0.17 g.) and triethylamine (0.23 g.) in EtOH (15 ml.) was heated under reflux for 7 hours. The solvent was evaporated and the residue was treated with sodium bicarbonate solution and extracted with EtOAc. The extract was dried (MgSO4) and evaporated to give an oil which was purified by medium pressure chromatography, eluting with 7.5% v/v MeOH in methylene chloride to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[5-cyanomethylaminopentyl]pyrimidine as a pale yellow solid which was used without further purification.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. customThe solvent was evaporated
  4. additionthe residue was treated with sodium bicarbonate solution
  5. extractionextracted with EtOAc
  6. dry with materialThe extract was dried (MgSO4)
  7. customevaporated
  8. customto give an oil which
  9. customwas purified by medium pressure chromatography
  10. washeluting with 7.5% v/v MeOH in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-3346560e8d47419bb730002ae812ffd8
Quelldatensatz
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04460584

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