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4,5-Diaminopyrimidine → HCID 178424861, Verbindung

HRID 1858099
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1858099
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([N:27]=[C:28]=S)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:40][C:41]1[C:46]([NH2:47])=[CH:45][N:44]=[CH:43][N:42]=1>[Hg]=O>[NH3:8].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([NH:27][C:28]3[NH:40][C:41]4[C:46]([N:47]=3)=[CH:45][N:44]=[CH:43][N:42]=4)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 837034,5-DiaminopyrimidineHCID 54130839HCID 54130839, Verbindung

Produkt 2

HCID 222AmmoniaHCID 178424861HCID 178424861, VerbindungAusbeute 8,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 30856Mercuric oxideKatalysator

Versuchsvorschrift

To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-isothiocyanato-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (210 mg in 5 mL toluene) was added 250 mg mercury(II) oxide followed by 130 mg 4,5-diaminopyrimidine and the mixture heated to reflux on an oil bath. After 48 hours, the mixture was cooled to room temperature and the reaction quenched by the addition of 2N hydrochloric acid (4 mL). The solvents were removed in vacuo and the residue treated with 2N ammonia in methanol (10 mL) then concentrated once again. The residue was washed with chloroform and the solids removed by filtration. Concentration of the organics and purification by flash chromatography on silica gel (ethyl acetate:hexane, 1:1; then chloroform:2N ammonia in methanol, 9:1) gave the title compound (10 mg).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. customthe reaction quenched by the addition of 2N hydrochloric acid (4 mL)
  4. customThe solvents were removed in vacuo
  5. additionthe residue treated with 2N ammonia in methanol (10 mL)
  6. concentrationthen concentrated once again
  7. washThe residue was washed with chloroform
  8. customthe solids removed by filtration
  9. customConcentration of the organics and purification by flash chromatography on silica gel (ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-deb8ecf52c49440390ddc8b4797da974
Quelldatensatz
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06150352

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