2-Amino-3-methylpyrazine → 2-Cyclopropyl-8-methylimidazo[1,2-a]pyrazine

HRID 869600

Reaktionsgleichung

Reaktionsgleichung von HRID 869600
[CH3:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][N:7]=1.Br[CH2:10][C:11]([CH:13]1[CH2:15][CH2:14]1)=O.C(=O)([O-])O.[Na+]>COCCOC.C1COCC1>[CH:13]1([C:11]2[N:8]=[C:3]3[C:2]([CH3:1])=[N:7][CH:6]=[CH:5][N:4]3[CH:10]=2)[CH2:15][CH2:14]1

Komponenten

6

Edukt 3

HCID 3022842-Amino-3-methylpyrazineHCID 516892Sodium BicarbonateHCID 109208412-Bromo-1-cyclopropylethan-1-one

Produkt 1

HCID 867214522-Cyclopropyl-8-methylimidazo[1,2-a]pyrazineAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

[step 1] 3-Methylpyrazin-2-amine (16 g, 147 mmol) was dissolved in 1,2-dimethoxyethane (122 mL) and THF (61 mL), 2-bromo-1-cyclopropylethanone (36 g, 220 mmol) was added, and the mixture was stirred at room temperature for 70 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the mixture, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-85/15 v/v) to give 2-cyclopropyl-8-methylimidazo[1,2-a]pyrazine (11g, 43%).

Aufarbeitung

  1. extractionthe mixture was extracted 3 times with chloroform
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-85/15 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-4e043acd524d49a8b1e0e2c908309b0c
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969345B2

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