Toluene → 4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl 2,2-dimethylpropanoate

HRID 347451

Reaktionsgleichung

Reaktionsgleichung von HRID 347451
[C:1]([O:7][C:8]1[C:9]([CH3:18])=[C:10]2[N:15]([CH:16]=1)[N:14]=[CH:13][NH:12][C:11]2=O)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].P(Cl)(Cl)([Cl:21])=O.CCN(C(C)C)C(C)C.C1(C)C=CC=CC=1>C(OCC)(=O)C.O>[C:1]([O:7][C:8]1[C:9]([CH3:18])=[C:10]2[N:15]([CH:16]=1)[N:14]=[CH:13][N:12]=[C:11]2[Cl:21])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1356205694-Hydroxy-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl 2,2-dimethylpropanoate

Produkt 1

HCID 210816794-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl 2,2-dimethylpropanoateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a mixture of 5-methyl-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-6-yl pivalate (300 mg, 1.20 mmol), phosphorus oxychloride (2.0 mL, 21.4 mmol) and DIEA (0.5 mL, 2.80 mmol) was added toluene (10 mL). The reaction was heated at 110° C. for 4 hours and then cooled to room temperature. The mixture was diluted with ethyl acetate (10 mL) and water (5 mL). The organic layer was separated and dried with sodium sulfate, concentrated in vacuo and purified by silica gel flash chromatography (eluted with 1–25% EtOAc/CH2Cl2) to give the title compound (250 mg, 78%) as a white solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel flash chromatography (eluted with 1–25% EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-6c1996030b3b412ca996c70ff1ec672d
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

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