Ethanol → 2,6-Diphenylpyrimidin-4-ol

HRID 269752

Reaktionsgleichung

Reaktionsgleichung von HRID 269752
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].C(O[C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C.[CH2:24]([OH:26])[CH3:25]>O>[C:3]1([C:2]2[NH:10][C:24](=[O:26])[CH:25]=[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:9]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 7165Ethyl benzoateHCID 14798Sodium HydroxideHCID 80289Benzamidine, hydrochloride

Produkt 1

HCID 1354755602,6-Diphenylpyrimidin-4-olAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Benzamidine hydrochloride (3.9 g, 24.9 mmol) was dissolved in a minimal amount of H2O (10 mL), to this was added sodium hydroxide pellets (1.0 g, 24.9 mmol, 1 eq.) dissolved in H2O (2 mL), followed by ethylbenzoate (4.53 mL, 26.1 mmol, 1.05 eq.). Ethanol was then added until a clear solution was obtained. The reaction mixture was then allowed to stir at room temperature overnight yielding a thick suspension, which was then filtered to give a white solid. After washing with diethyl ether to remove unreacted/excess β-ketoester the solid was dried in vacuo to give 57% of the desired product. 1H NMR δ (DMSO-d6): 8.31-8.18 (m, 5H, Ar), 7.60-7.54 (m, 5H, Ar), 6.92 (s, 1H, Ar).

Aufarbeitung

  1. customwas obtained
  2. customyielding a thick suspension, which
  3. filtrationwas then filtered
  4. customto give a white solid
  5. washAfter washing with diethyl ether
  6. customto remove unreacted/excess β-ketoester the solid
  7. customwas dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cca8d7fe9ff543c59b437f796407218b
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449470B2

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