Sodium Carbonate → 6-[1-(1-Ethoxyethyl)-1H-pyrazol-4-yl]-1,2,4-triazin-3-amine

HRID 500237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500237
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[N:13]=[N:12][C:11]([NH2:14])=[N:10][CH:9]=1.[CH2:15]([O:17][CH:18]([N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1)[CH3:19])[CH3:16]>O.C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([O:17][CH:18]([N:20]1[CH:24]=[C:23]([C:8]2[N:13]=[N:12][C:11]([NH2:14])=[N:10][CH:9]=2)[CH:22]=[N:21]1)[CH3:19])[CH3:16]

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 153325646-Bromo-1,2,4-triazin-3-amineHCID 467367981-(1-Ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Produkt 1

HCID 672245336-[1-(1-Ethoxyethyl)-1H-pyrazol-4-yl]-1,2,4-triazin-3-amineAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Sodium carbonate (510 mg, 4.8 mmol) in water (1 mL) was added to a mixture of 6-bromo-1,2,4-triazin-3-amine (0.420 g, 2.40 mmol), 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.766 g, 2.88 mmol), and tetrakis(triphenylphosphine)palladium (100 mg, 0.1 mmol) in toluene (7 mL) and ethanol (5 mL). The resulting mixture was heated at 110° C. for 2 h. The mixture was cooled to RT, diluted with water, and extracted with chloroform. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was treated with CH2Cl2/Et2O and filtered to give the desired product (0.39 g, 69%). LCMS: (M+H)=235.4.

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with chloroform
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe residue was treated with CH2Cl2/Et2O
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-9999ed8e98284d5db871256409a8c210
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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