Guanidine → {1-[4-(2-Amino-5-phenyl-pyrimidin-4-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

HRID 2362166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2362166
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20]N(C)C)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH2:32][C:33]([NH2:35])=[NH:34].CO[Na]>CN(C=O)C.CC(=O)OCC>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][N:32]=[C:33]([NH2:35])[N:34]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 3520GuanidineHCID 66719111HCID 66719111, VerbindungHCID 178418582HCID 178418582, Verbindung

Produkt 1

HCID 66823192{1-[4-(2-Amino-5-phenyl-pyrimidin-4-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl EsterAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of compound 1 (3 g, 7.2 mmol) and guanidine (2 g, 35 mmol) in DMF (15 mL) was added MeONa (1.8 g, 35 mmol) and the mixture was heated to 100° C. and stirred for 4 h. The solution was cooled to r.t. and diluted with 80 mL of EA. The organic phase was washed with 0.1N HClaq and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatography to give 2.1 g of 5-1 as a yellow solid.

Aufarbeitung

  1. temperatureThe solution was cooled to r.t.
  2. washThe organic phase was washed with 0.1N HClaq and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-696a31ff9ca34d578fd78eef1034b599
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691825B2

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