Methanol → 5-Ethynyl-6-methylpyridin-2-amine

HRID 78195

Reaktionsgleichung

Reaktionsgleichung von HRID 78195
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[C:9]#[C:10][Si](C)(C)C.CO.C(=O)([O-])[O-].[K+].[K+]>O>[C:9]([C:3]1[CH:4]=[CH:5][C:6]([NH2:8])=[N:7][C:2]=1[CH3:1])#[CH:10]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 592552326-Methyl-5-trimethylsilanylethynyl-pyridin-2-ylamine

Produkt 1

HCID 552859385-Ethynyl-6-methylpyridin-2-amineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 6-methyl-5-trimethylsilanylethynyl-pyridin-2-ylamine (450 mg, 1.9 mmol) described in Manufacturing Example 187-1-1 and methanol (5 mL) was added potassium carbonate (390 mg, 2.8 mmol), which was stirred for 30 minutes at the same temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (220 mg, 88%).

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. concentrationwas concentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0106c4cd6f4b4a95b3cae1e3d2faafcc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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