Methyl iodide → HCID 57747383, Verbindung

HRID 386642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386642
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][C:10]2[C:11]3[NH:34][CH:33]=[CH:32][C:12]=3[N:13]=[C:14]([N:16]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:15]=2)=[C:4]([CH3:35])[CH:3]=1.[Li+].[CH3:37][Si]([N-][Si](C)(C)C)(C)C.IC>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:35])[C:5]([S:9][C:10]2[C:11]3[N:34]([CH3:37])[CH:33]=[CH:32][C:12]=3[N:13]=[C:14]([N:16]([C:24]3[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=3)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:15]=2)=[C:6]([CH3:8])[CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 57747382HCID 57747382, Verbindung

Produkt 1

HCID 57747383HCID 57747383, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cold mixture of tert-butyl 4-(4-bromo-2,6-dimethylphenylthio)-5H-pyrrolo[3,2-d]pyrimidin-2-yl(4-cyanophenyl)carbamate (1.5 mmol) in THF (5 ml) at −78° C. is added a solution of LiHMDS (2 mmol). The mixture is warmed to 0° C. over 2 hours and then cooled to −78° C. Iodomethane (6 mmol) is added and the mixture warmed to room temperature over 2 hours and then stirred at room temperature for an additional 2 hours. The mixture is washed with brine and extracted with ethyl acetate (×3). The combined organic layers are dried over MgSO4 and concentrated to dryness. The crude material is purified by chromatography on silica.

Aufarbeitung

  1. temperaturecooled to −78° C
  2. temperaturethe mixture warmed to room temperature over 2 hours
  3. washThe mixture is washed with brine
  4. extractionextracted with ethyl acetate (×3)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe crude material is purified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-e829f80cd66345a2bacb2348eb29615a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372852B2

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