4-Fluorophenyl isothiocyanate → 3-(4-Fluorophenyl)-2-thioxo-2,3-dihydropyrido[3,2-d]pyrimidin-4(1H)-one

HRID 408830

Reaktionsgleichung

Reaktionsgleichung von HRID 408830
[NH2:1][C:2]1[C:3]([C:8]([O:10]CC)=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[S:22])=[CH:16][CH:15]=1>N1C=CC=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:8](=[O:10])[C:3]3[N:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][C:21]2=[S:22])=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 152414-Fluorophenyl isothiocyanateHCID 565054Ethyl 3-aminopyridine-2-carboxylate

Produkt 1

HCID 576141483-(4-Fluorophenyl)-2-thioxo-2,3-dihydropyrido[3,2-d]pyrimidin-4(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A mixture of ethyl 3-aminopyridine-2-carboxylate (2.0 g, 12.0 mmol) and 4-fluorophenylisothiocyanate (1.84 g, 12.0 mmol) in 7 mL of anhydrous pyridine is stirred at 45° C. for 21 h. After cooling, the pyridine is evaporated in vacuo, and ice water is added to the residue. The resulting mixture is slurried in EtOAc and filtered to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.59 (1H, m), 7.79 (2H, m), 7.33 (4H, m).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe pyridine is evaporated in vacuo, and ice water
  3. additionis added to the residue
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-c5235bf44fe247beb342bde1ae6c455c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759361B2

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