Lithium Hexamethyldisilazide → HCID 57747371, Verbindung

HRID 386624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386624
[Br:1][C:2]1[CH:33]=[C:32]([CH3:34])[C:5]([O:6][C:7]2[C:8]3[NH:31][CH:30]=[CH:29][C:9]=3[N:10]=[C:11]([N:13]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:12]=2)=[C:4]([CH3:35])[CH:3]=1.[Li+].[CH3:37][Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:35])[C:5]([O:6][C:7]2[C:8]3[N:31]([CH3:37])[CH:30]=[CH:29][C:9]=3[N:10]=[C:11]([N:13]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:12]=2)=[C:32]([CH3:34])[CH:33]=1

Komponenten

4

Edukt 2

HCID 2733832Lithium HexamethyldisilazideHCID 57747399HCID 57747399, Verbindung

Produkt 1

HCID 57747371HCID 57747371, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cold mixture of tert-butyl 4-(4-bromo-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-yl(4-cyanophenyl)carbamate (0.81 g, 1.5 mmol) in THF (5 ml) at −78° C. was added a solution of LiHMDS (1M, 2 ml, 2 mmol). The mixture was warmed to 0° C. over 2 hours and then was cooled to −78° C. Idomethane (0.37 ml, 6 mmol) was added and the mixture was warmed to room temperature over 2 hours and then stirred at this temperature for an additional 2 hours. The mixture was washed with brine, extracted with ethyl acetate (×3). The organic layers were combined dried over MgSO4 and concentrated to dryness. The crude material was purified by chromatography on silica to obtain the title compound (0.782 g, 1.42 mmol, 95%). 1H NMR (CDCl3, 400 MHz) δ 1.32 (s, 9H), 2.07 (s, 6H), 4.18 (s, 3H), 6.65 (d, J=3.8 Hz, 1H), 7.15 (d, J=8.8 Hz, 2H), 7.21 (s, 2H), 7.37 (d, J=3.8 Hz, 1H), 7.49 (d, J=8.8, 2H).

Aufarbeitung

  1. temperaturewas cooled to −78° C
  2. additionIdomethane (0.37 ml, 6 mmol) was added
  3. temperaturethe mixture was warmed to room temperature over 2 hours
  4. washThe mixture was washed with brine
  5. extractionextracted with ethyl acetate (×3)
  6. dry with materialThe organic layers were combined dried over MgSO4
  7. concentrationconcentrated to dryness
  8. customThe crude material was purified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-8f02c6e9664c4a229a53b64e6964bd84
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372852B2

Notizen zur Reaktion

Wird geladen…