Water → HCID 57940470, Verbindung

HRID 1437114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437114
C([N:4]1[CH2:10][C:9]([CH3:12])([CH3:11])[C:8](=[O:13])[N:7]([CH3:14])[C:6]2[CH:15]=[N:16][C:17]([Cl:19])=[N:18][C:5]1=2)C=C.O>O1CCOCC1>[Cl:19][C:17]1[N:16]=[CH:15][C:6]2[N:7]([CH3:14])[C:8](=[O:13])[C:9]([CH3:11])([CH3:12])[CH2:10][NH:4][C:5]=2[N:18]=1

Komponenten

4

Edukt 2

HCID 962WaterHCID 86621279HCID 86621279, Verbindung

Produkt 1

HCID 57940470HCID 57940470, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

9-allyl-2-chloro-8,9-dihydro-5,7,7-trimethyl-5H-pyrimido[4,5-b][1,4]diazepin-6(7H)-one (1.21 g, 4.34 mmol, prepared by method C) and dichloro(2,7-dimethyl-octa-2,6-diene-1,8-yl) ruthenium (IV) (0.26 g, 0.43 mmol, prepared following Tetrahedron Letters, 1965, 47, 4187) were suspended in dioxane (10 mL) and water (30 mL) in a pressure tube. The resultant suspension was stirred at 100° C. over two nights. The reaction was allowed to cool to room temperature and filtered through celite. The celite was washed copiously with water and DCM. The combined filtrates were concentrated under reduced pressure and partitioned between brine and DCM. The aqueous layer was extracted with dichloromethane (5×20 mL) and the combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to give a brown gum. This gum was purified by column chromatography (50% EtOAc in hexanes, loaded on silica, ˜100 mL silica) to give a white solid, which was triturated with diethyl ether. The solid was collected by filtration and washed with diethyl ether (1×2 mL) and pentane (3×2 mL) to give a cream powder (351 mg, 34% yield). NMR DMSO D6 1.09 (6H, s), 3.22 (3H, s), 3.25 (2H, d), 8.08 (1H, s), 8.48 (1H, br d); MS (ES+) 241.

Aufarbeitung

  1. filtrationfiltered through celite
  2. washThe celite was washed copiously with water and DCM
  3. concentrationThe combined filtrates were concentrated under reduced pressure
  4. custompartitioned between brine and DCM
  5. extractionThe aqueous layer was extracted with dichloromethane (5×20 mL)
  6. dry with materialthe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a brown gum
  10. customThis gum was purified by column chromatography (50% EtOAc in hexanes, loaded on silica, ˜100 mL silica)
  11. customto give a white solid, which
  12. customwas triturated with diethyl ether
  13. filtrationThe solid was collected by filtration
  14. washwashed with diethyl ether (1×2 mL) and pentane (3×2 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5a52b83ac0084d95805dc726f111675f
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622463B2

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