Sodium hydride → HCID 86695236, Verbindung

HRID 1504081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504081
Cl[C:2]1[C:3]2[CH:10]=[C:9]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[CH3:23][N:24]([CH3:32])[CH:25]1[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]1>C1COCC1>[CH3:23][N:24]([CH3:32])[CH:25]1[CH2:30][CH2:29][CH:28]([O:31][C:2]2[C:3]3[CH:10]=[C:9]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:27][CH2:26]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 18702099trans-4-(Dimethylamino)cyclohexanolHCID 86695235HCID 86695235, Verbindung

Produkt 1

HCID 86695236HCID 86695236, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl N-(2-[4-chlorothieno[2,3-d]pyrimidin-6-yl]ethyl)carbamate (100 mg, 0.32 mmol, 1.00 equiv) in freshly distilled THF (20 mL) was added sodium hydride (64 mg, 1.6 mmol, 5.0 equiv, 60% dispersion in mineral oil) at 0° C. under nitrogen. After stirring for 30 min at room temperature, a solution of 4-(dimethylamino)cyclohexan-1-ol (50 mg, 0.35 mmol, 1.06 equiv) was added and stirred overnight at room temperature. The reaction was then quenched by the addition of brine and extracted with EtOAc. The organic layers was combined and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was applied onto a silica gel column with DCM/MeOH (50:1-30:1) to provide 70 mg (52%) of tert-butyl N-[2-(4-[[4-(dimethylamino)cyclohexyl]oxy]thieno[2,3-d]pyrimidin-6-yl)ethyl]carbamate as a light yellow solid. MS (ES): m/z 421 (M+H)+.

Aufarbeitung

  1. stirringstirred overnight at room temperature
  2. customThe reaction was then quenched by the addition of brine
  3. extractionextracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration

Quellen und Nachweise

ORD-Eintrag
ord-c220d2064788407c8d2662360e30d36d
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212190B2

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