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Ethanol → N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-amine

HRID 1811825
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1811825
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16]2[C:23]([C:24]3[N:29]=[C:28]([CH3:30])[N:27]=[C:26]([S:31][CH3:32])[N:25]=3)=[CH:22][C:19]([CH:20]=O)=[CH:18][N:17]=2)=[CH:11][CH:10]=1.CCO.C([BH3-])#N.[Na+]>CC(O)=O.O.CCOC(C)=O>[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16]2[C:23]([C:24]3[N:29]=[C:28]([CH3:30])[N:27]=[C:26]([S:31][CH3:32])[N:25]=3)=[CH:22][C:19]([CH2:20][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:18][N:17]=2)=[CH:11][CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 702EthanolHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 866470496-(6-Methoxypyridin-3-ylamino)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)nicotinaldehyde

Produkt 1

HCID 66612061N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-amineAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Morpholine (0.018 mL, 0.204 mmol) and a few drops of AcOH (3.88 μL, 0.068 mmol) were added to a stirred suspension of 6-(6-methoxypyridin-3-ylamino)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)nicotinaldehyde (25 mg, 0.068 mmol) in EtOH (3.00 mL, 51.4 mmol), the mixture was stirred at room temperature for 1 h, then treated with sodium cyanoborohydride (4.26 mg, 0.068 mmol) and stirred at room temperature overnight. The mixture was diluted with water and EtOAc (10mL each). The separated aqueous layer was extracted with ethyl acetate (2×10 mL) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give crude product which was purified by flash column chromatography (ISCO CombiFlash®, Teledyne ISCO, Lincoln, Nebr., DCM to 10% DCM in MeOH) to give N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-amine (19 mg, 0.043 mmol, 63.7% yield) as a yellow solid. LCMS (API-ES) m/z 440 (M+H)+.

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. extractionThe separated aqueous layer was extracted with ethyl acetate (2×10 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product which
  7. customwas purified by flash column chromatography (ISCO CombiFlash®, Teledyne ISCO, Lincoln, Nebr., DCM to 10% DCM in MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-77f9f4c2d6aa468d9c496b4653bb1440
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08362241B2

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