Hydrochloric Acid → HCID 21891690, Verbindung

HRID 858082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 858082
[CH2:1]([N:5]1[C:10]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[CH:9][C:8](=[O:23])[N:7]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[C:6]1=[O:32])[CH2:2][CH2:3][CH3:4].[N:33](OCCC(C)C)=O.Cl>C(O)C>[CH2:1]([N:5]1[C:10]2[N:11]=[C:12]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=3)[NH:33][C:9]=2[C:8](=[O:23])[N:7]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[C:6]1=[O:32])[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 218918031-butyl-3-(2-fluorobenzyl)-6-[2-(4-nitro-phenyl)-ethylamino]-1H-pyrimidine-2,4-dione

Produkt 1

HCID 21891690HCID 21891690, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

1-Butyl-3-(2-fluorobenzyl)-6-[2-(4-nitro-phenyl)-ethylamino]-1H-pyrimidine-2,4-dione (2.3 g, 5.2 mmol) was dissolved in ethanol (20 mL) and treated with isoamyl nitrite (Aldrich) (3.6 mL, 26 mmol). Concentrated aqueous hydrochloric acid (1 mL) was added to the reaction mixture. The reaction was stirred at 23° C. for 40 minutes. The ethanol was removed under reduced pressure and the residue washed with diethyl ether. The solid residue was then dissolved in n-butanol (15 mL), and the mixture refluxed for 30 minutes. After cooling to room temperature 1-butyl-3-(2-fluorobenzyl)-6-[2-(4-nitro-phenyl)-ethylamino]-1H-pyrimidine-2,4-dione separated as pale yellow crystals which were collected by filtration (1.91 g, 81%). LCMS, m/z(M+H)=452.24.

Aufarbeitung

  1. customThe ethanol was removed under reduced pressure
  2. washthe residue washed with diethyl ether
  3. dissolutionThe solid residue was then dissolved in n-butanol (15 mL)
  4. temperaturethe mixture refluxed for 30 minutes
  5. temperatureAfter cooling to room temperature 1-butyl-3-(2-fluorobenzyl)-6-[2-(4-nitro-phenyl)-ethylamino]-1H-pyrimidine-2,4-dione
  6. customseparated as pale yellow crystals which
  7. filtrationwere collected by filtration (1.91 g, 81%)

Quellen und Nachweise

ORD-Eintrag
ord-18601a50567647f89e276a629fddef38
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148229B2

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