Ethyl 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarboxylate → Ethyl 6-oxo-2-(((tetrahydrofuran-2-yl)methyl)amino)-1,6-dihydropyrimidine-5-carboxylate

HRID 626457

Reaktionsgleichung

Reaktionsgleichung von HRID 626457
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][NH2:7].CS[C:10]1[NH:11][C:12](=[O:21])[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:15]=1>CO>[O:21]=[C:12]1[NH:11][C:10]([NH:7][CH2:6][CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)=[N:15][CH:14]=[C:13]1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Komponenten

4

Edukt 2

HCID 239049Ethyl 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarboxylateHCID 253298Tetrahydrofurfurylamine

Produkt 1

HCID 17229209Ethyl 6-oxo-2-(((tetrahydrofuran-2-yl)methyl)amino)-1,6-dihydropyrimidine-5-carboxylateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(tetrahydrofuran-2-yl)methanamine (142 mg, 1.40 mmol) was added into ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrmidine-5-carboxylate (300 mg, 1.40 mmol) in methanol and refluxed overnight. After half of the starting material was consumed, the reaction mixture was reheated again overnight. Then the reaction mixture was cooled and the precipitate filtered. 1H-NMR confirmed the product as ethyl 6-oxo-2-(((tetrahydrofuran-2-yl)methyl)amino)-1,6-dihydropyrimidine-5-carboxylate (HGN-0017) (176 mg, 47% yield).

Aufarbeitung

  1. temperaturerefluxed overnight
  2. customAfter half of the starting material was consumed
  3. temperatureThen the reaction mixture was cooled
  4. filtrationthe precipitate filtered

Quellen und Nachweise

ORD-Eintrag
ord-48636987876e47b1832aee1079518157
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309232B2

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