Sodium Hydroxide → HCID 178429605, Verbindung

HRID 44394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 44394
C([NH:9][C:10](=[O:27])[NH:11][C:12]1[S:16][C:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:14]([CH3:24])[C:13]=1[C:25]#[N:26])(=O)C1C=CC=CC=1.[OH-].[Na+]>CCO>[NH2:26][C:25]1[C:13]2[C:14]([CH3:24])=[C:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:16][C:12]=2[NH:11][C:10](=[O:27])[N:9]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 57456933Tert-butyl 5-(3-benzoylureido)-4-cyano-3-methylthiophene-2-carboxylate

Produkt 1

HCID 178429605HCID 178429605, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of tert-butyl 5-(3-benzoylureido)-4-cyano-3-methylthiophene-2-carboxylate (example 64a) (18 g, 60.52 mmol) in EtOH (200 mL) was added NaOH (75 mL, 2N). The suspension became clear, and the mixture was heated to reflux for 30 min. After cooling to rt, the reaction was filtered, and the filtrate was cooled to 0° C. in an ice/water bath. The solution was neutralized with 10% acetic acid. The precipitated solid was collected by filtration, and heated in EtOH at 80° C. under N2 for 20 min. After cooling to rt, the product was collected by filtration and washed with 10% EtOH in H2O to yield tert-Butyl 4-amino-5-methyl-2-oxo-1,2-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (10.73 g, 63%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ1.51 (s, 9H), 2.73 (s, 3H), 3.18 (s, 2H). MS 282.2 (MH+).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 min
  3. filtrationthe reaction was filtered
  4. temperaturethe filtrate was cooled to 0° C. in an ice/water bath
  5. filtrationThe precipitated solid was collected by filtration
  6. temperatureheated in EtOH at 80° C. under N2 for 20 min
  7. temperatureAfter cooling to rt
  8. filtrationthe product was collected by filtration
  9. washwashed with 10% EtOH in H2O

Quellen und Nachweise

ORD-Eintrag
ord-3db84ec6624f462aa8b65ccad99aedb7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541421B2

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