Toluene → 6-[3,5-Bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-2-(methylthio)-5-oxo-4-phenylpyrimido[4,5-b][1,5]diazocine

HRID 1829643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1829643
[C:1]1(OB(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[F:24][C:25]([F:54])([F:53])[C:26]1[CH:27]=[C:28]([CH:46]=[C:47]([C:49]([F:52])([F:51])[F:50])[CH:48]=1)[CH2:29][N:30]1[CH2:37][CH2:36][CH2:35][NH:34][C:33]2[N:38]=[C:39]([S:43][CH3:44])[N:40]=[C:41](Cl)[C:32]=2[C:31]1=[O:45]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[F:24][C:25]([F:54])([F:53])[C:26]1[CH:27]=[C:28]([CH:46]=[C:47]([C:49]([F:52])([F:51])[F:50])[CH:48]=1)[CH2:29][N:30]1[CH2:37][CH2:36][CH2:35][NH:34][C:33]2[N:38]=[C:39]([S:43][CH3:44])[N:40]=[C:41]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:32]=2[C:31]1=[O:45]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 220535996-[3,5-Bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine

Produkt 1

HCID 220535696-[3,5-Bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-2-(methylthio)-5-oxo-4-phenylpyrimido[4,5-b][1,5]diazocineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Phenylboric acid (732 mg), tetrakis(triphenylphosphine)palladium (289 mg), toluene (15 ml), 1,4-dioxane (8 ml) and a 2 mol/L aqueous solution of sodium carbonate (15 ml) were added to 6-[3,5-bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine (Compound of Reference Example 7; 2.43 g). While heated, the mixture was refluxed for 5 hours under a stream of argon gas. Subsequently, the reaction mixture was diluted with ethyl acetate, was washed with a 2 mol/L aqueous solution of sodium carbonate, and was then dried over anhydrous sodium sulfate. The solvent was removed and the resulting residue was purified on a silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 6-[3,5-bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-2-(methylthio)-5-oxo-4-phenylpyrimido[4,5-b][1,5]diazocine (2.63 g, 100%).

Aufarbeitung

  1. temperatureWhile heated
  2. temperaturethe mixture was refluxed for 5 hours under a stream of argon gas
  3. washwas washed with a 2 mol/L aqueous solution of sodium carbonate
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customthe resulting residue was purified on a silica gel column chromatography (ethyl acetate:hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-87b3696e791a4543aef3f487b9f81615
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064119B2

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