Methyl iodide → HCID 89782099, Verbindung

HRID 1056257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056257
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[N:8]=[CH:7]2.[H-].[Na+].[CH3:19]I>C1COCC1.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:19])[N:8]=[CH:7]2

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 897819638-bromo-N-tert-butylquinazolin-2-amine

Produkt 1

HCID 89782099HCID 89782099, VerbindungAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

8-Bromo-N-(tert-butyl)quinazolin-2-amine (374a) (40 mg, 0.14 mmol) in THF (4 mL) at 0° C. was treated with NaH (60% dispersion in mineral oil, 8.6 mg, 0.21 mmol) and stirred at 0° C. for 30 min. MeI (10.71 μl, 0.17 mmol) was added and the solution was warmed to RT overnight (16 h). The reaction mixture was treated with brine and extracted with EtOAc (50 mL), dried over MgSO4, filtered and concentrated. Purification on a silica gel column (0-50% EtOAc in hexanes) afforded the title compound (34 mg, 0.12 mmol, 82% yield) as yellow viscous oil. m/z (ESI, +ve ion) 294.0/296.0 (M+H)+.

Aufarbeitung

  1. temperaturethe solution was warmed to RT overnight (16 h)
  2. extractionextracted with EtOAc (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on a silica gel column (0-50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6e79ecb1091b44bebf1f434691772157
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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