Methyl iodide → 6-[3,5-Bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-10-methyl-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine

HRID 1829642

Reaktionsgleichung

Reaktionsgleichung von HRID 1829642
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][NH:11][C:10]2[N:15]=[C:16]([S:20][CH3:21])[N:17]=[C:18]([Cl:19])[C:9]=2[C:8]1=[O:22].[H-].[Na+].[CH3:34]I>CN(C)C=O.C(OCC)(=O)C>[F:29][C:26]([F:27])([F:28])[C:24]1[CH:23]=[C:5]([CH:4]=[C:3]([C:2]([F:30])([F:1])[F:31])[CH:25]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][N:11]([CH3:34])[C:10]2[N:15]=[C:16]([S:20][CH3:21])[N:17]=[C:18]([Cl:19])[C:9]=2[C:8]1=[O:22]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 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 220536006-[3,5-Bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-10-methyl-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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; 1.50 g) was dissolved in N,N-dimethylformamide (6 mL). To this solution, sodium hydride (185 mg, 60% oil suspension) was added and the mixture was stirred at room temperature for 1 hour. Methyl iodide (0.4 mL) was then added and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, was sequentially washed with water and a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate. Following removal of the solvent, the residue was purified on a silica gel column-chromatography (ethyl acetate:hexane=1:1) to obtain 6-[3,5-bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-10-methyl-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine (1.36 g, 88%).

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature for 1 hour
  2. washwas sequentially washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate
  4. customremoval of the solvent
  5. customthe residue was purified on a silica gel column-chromatography (ethyl acetate:hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-6bfc8deeb9894ee9b8e23c9ff6aea477
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064119B2

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