Diisopropylethylamine → tert-butyl 4-fluoro-2-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)phenylcarbamate

HRID 605865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605865
[NH2:1][CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:11]([NH:23][C:24]2[N:29]=[C:28](SC#N)[C:27]([N+:33]([O-:35])=[O:34])=[CH:26][N:25]=2)[CH:10]=1.C(N(CC)C(C)C)(C)C>C1COCC1.CCOC(C)=O>[C:18]([O:17][C:16](=[O:22])[NH:15][C:12]1[CH:13]=[CH:14][C:9]([F:8])=[CH:10][C:11]=1[NH:23][C:24]1[N:25]=[C:26]([NH:1][CH:2]2[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)[C:27]([N+:33]([O-:35])=[O:34])=[CH:28][N:29]=1)([CH3:21])([CH3:19])[CH3:20]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 59704889tert-Butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamate

Produkt 1

HCID 59705007tert-butyl 4-fluoro-2-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)phenylcarbamateAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To the solution of 96 mg (0.95 mmol) of 4-amino-tetrahydropyran in 35 mL anhydrous THF was added 0.35 g (0.86 mmol) tert-butyl 4-fluoro-2-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)phenylcarbamate, then 0.3 mL N,N-diisopropylethyl amine (1.7 mmol). The slightly cloudy mixture was stirred at room temperature for 3 hrs till HPLC showed the completion of reaction. The mixture became clear then. The reaction mixture was diluted with EtOAc, washed with brine twice, and then dried over Na2SO4. Solvents were removed under vacuum to give 0.28 g (˜70% yield) orange-yellow solid as the crude product.

Aufarbeitung

  1. customthe completion of reaction
  2. washwashed with brine twice
  3. dry with materialdried over Na2SO4
  4. customSolvents were removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-14ce2b311d8d4f90aa2907749485698d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915268B2

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