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

HRID 1811823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811823
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[O:11]1[CH2:15][CH2:14][O:13][CH:12]1[C:16]1[CH:17]=[C:18]([C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([S:30][CH3:31])[N:24]=2)[C:19](F)=[N:20][CH:21]=1.[NH2:32][C:33]1[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[N:37][CH:38]=1.C1COCC1>[NH4+].[Cl-].O.C(OCC)(=O)C>[O:11]1[CH2:15][CH2:14][O:13][CH:12]1[C:16]1[CH:17]=[C:18]([C:23]2[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([S:30][CH3:31])[N:24]=2)[C:19]([NH:32][C:33]2[CH:38]=[N:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)=[N:20][CH:21]=1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 811216-Methoxy-3-pyridinylamineHCID 2733832Lithium HexamethyldisilazideHCID 595484572-(5-(1,3-Dioxolan-2-yl)-2-fluoropyridin-3-yl)-4-methyl-6-(methylthio)-1,3,5-triazine

Produkt 1

HCID 666112635-(1,3-dioxolan-2-yl)-N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyridin-2-amineAusbeute 6,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

LiHMDS (1.0 M in THF, 4.14 mL, 4.14 mmol) was added to a stirred solution of 2-(5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-yl)-4-methyl-6-(methylthio)-1,3,5-triazine (0.425 g, 1.379 mmol) and 5-amino-2-methoxypyridine (0.257 g, 2.068 mmol) in THF (3.00 mL, 36.6 mmol) at 0° C. and the mixture was stirred at the same temperature for 1 h. The reaction mixture was diluted with NH4Cl (aq) and water (10 mL each) and diluted with ethyl acetate (10 mL). The separated aqueous layer was extracted with ethyl acetate (2×10 mL) and the combined organic layers were washed with brine, dried over Na2SO4, concentrated and the residue was purified by flash column chromatography (ISCO CombiFlash®, Teledyne ISCO, Lincoln, Nebr., hexanes to 50% ethyl acetates in hexanes) to give 5-(1,3-dioxolan-2-yl)-N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyridin-2-amine (35 mg, 0.085 mmol, 6.15% yield) as a yellow solid. LCMS (API-ES) m/z 413 (M+H)+.

Aufarbeitung

  1. extractionThe separated aqueous layer was extracted with ethyl acetate (2×10 mL)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified by flash column chromatography (ISCO CombiFlash®, Teledyne ISCO, Lincoln, Nebr., hexanes to 50% ethyl acetates in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e01f978ae550454f80a4fb2aae400b2a
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362241B2

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