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Triethylamine → 2-(2-Acetylaminopyrimidin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

HRID 1890501
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1890501
C(N(CC)CC)C.[CH3:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]([C:19]2[C:20](=[S:25])[NH:21][CH:22]=[CH:23][CH:24]=2)=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1.[C:26]([NH:29][C:30]1[N:35]=[C:34]([CH2:36]Cl)[CH:33]=[CH:32][N:31]=1)(=[O:28])[CH3:27].C(OCC)(=O)C>CN(C)C=O>[C:26]([NH:29][C:30]1[N:35]=[C:34]([CH2:36][S:25][C:20]2[C:19]([C:17]([NH:16][C:11]3[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([CH3:8])[CH:10]=3)=[O:18])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:33]=[CH:32][N:31]=1)(=[O:28])[CH3:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 23151038N-(3,5-Dimethylphenyl)-2-thioxo-1,2-dihydropyridine-3-carboxamideHCID 451192602-Acetylamino-4-chloromethylpyrimidine

Produkt 1

HCID 119648552-(2-Acetylaminopyrimidin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Triethylamine (45 mL, 0.32 mmol) was added to a solution of N-(3,5-dimethylphenyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide (28 mg, 0.11 mmol, Reference Compound No. 13-1) and 2-acetylamino-4-(chloromethyl)pyrimidine (18 mg, 0.10 mmol, Reference Compound No. 11-1) in anhydrous N,N-dimethylformamide (1.0 mL) at room temperature, and the mixture was stirred for 16 hours. Ethyl acetate (30 mL) was added thereto, then the whole was washed with saturated aqueous sodium hydrogencarbonate solution (30 mL) and brine (30 mL), and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the precipitated solid was filtered off with diethyl ether and washed. The solid was dried at 50° C. under reduced pressure to give 21 mg of the target compound as a light orange solid (Yield: 52%).

Aufarbeitung

  1. washthe whole was washed with saturated aqueous sodium hydrogencarbonate solution (30 mL) and brine (30 mL)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe precipitated solid was filtered off with diethyl ether
  5. washwashed
  6. customThe solid was dried at 50° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3db15bbec82f4bf091a291be43c11b1c
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08507485B2

Notizen zur Reaktion

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