Hydrochloric Acid → 5-[5-Bromo-4-(4-hydroxy-butylsulfanyl)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide

HRID 1182056

Reaktionsgleichung

Reaktionsgleichung von HRID 1182056
[Br:1][C:2]1[C:3]([S:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[N:20][CH:21]=1.Cl.O>C(#N)C.O1CCOCC1.C(O)C>[Br:1][C:2]1[C:3]([S:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[N:4][C:5]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[N:20][CH:21]=2)=[N:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 223138505-Aminopyridine-2-sulfonamideHCID 589818994-(5-Bromo-2-chloro-pyrimidin-4-ylsulfanyl)-butan-1-ol

Produkt 1

HCID 589818375-[5-Bromo-4-(4-hydroxy-butylsulfanyl)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6342AcetonitrileLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

298 mg (1.0 mmol) of 4-(5-bromo-2-chloro-pyrimidin-4-ylsulfanyl)-butan-1-ol is dissolved in 2 ml of acetonitrile and added to a suspension of 172 mg (1.0 mmol) of 5-amino-pyridine-2-sulfonic acid amide (representation according to W. T. Caldwell, E. C. Kornfeld J Am. Chem. Soc. 1942, 64, 1695-1698) in 1 ml of acetonitrile, 0.25 ml of a 4 molar solution of hydrochloric acid in 1,4-dioxane as well as 0.25 ml of water. The reaction mixture is stirred under reflux for 24 hours. It is mixed with 1 ml of ethanol and stirred for another 24 hours under reflux. After cooling, the precipitate that is formed is filtered off, and the filtrate is concentrated by evaporation. The residue is purified by chromatography (Flashmaster II, DCM/MeOH 9:1). The crude product that is obtained is then purified by preoperative thin-layer chromatography. 43 mg (0.10 mmol, 10% of theory) of the product 5-[5-bromo-4-(4-hydroxy-butylsulfanyl)-pyrimidin-2-ylamino]-pyridine-2-sulfonic acid amide is obtained

Aufarbeitung

  1. temperatureunder reflux for 24 hours
  2. stirringstirred for another 24 hours
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. customthe precipitate that is formed
  6. filtrationis filtered off
  7. concentrationthe filtrate is concentrated by evaporation
  8. customThe residue is purified by chromatography (Flashmaster II, DCM/MeOH 9:1)
  9. customThe crude product that is obtained
  10. customis then purified by preoperative thin-layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8d84815d3e5543c283b1d91b213055dd
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288547B2

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