3-Amino-6-furan-2-yl-pyrazine-2-carboxylic acid methyl ester → 3-Amino-6-(tetrahydrofuran-2-yl)pyrazine-2-carboxylic acid methyl ester

HRID 2368318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2368318
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[N:6]=1)=[O:4]>C1COCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([CH:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[N:6]=1)=[O:4]

Komponenten

4

Edukt 1

HCID 700988573-Amino-6-furan-2-yl-pyrazine-2-carboxylic acid methyl ester

Produkt 1

HCID 700987903-Amino-6-(tetrahydrofuran-2-yl)pyrazine-2-carboxylic acid methyl esterAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-amino-6-furan-2-yl-pyrazine-2-carboxylic acid methyl ester (1.94 g, 8.9 mmol) was dissolved in THF (80 ml) and hydrogenated over night at rt in the presence of 10% Pd/C (1.0 g). The catalyst was filtered and washed with THF. The filtrate was again hydrogenated in the presence of Pd/C 10% (1.0 g) overnight. The catalyst was filtered and washed with THF. The filtrate was concentrated. The crude product was purified by column chromatography using a CH2Cl2/MeOH gradient for elution, providing the title compound (611 mg, 31%) as yellow solid.

Aufarbeitung

  1. filtrationThe catalyst was filtered
  2. washwashed with THF
  3. customwas again hydrogenated in the presence of Pd/C 10% (1.0 g) overnight
  4. filtrationThe catalyst was filtered
  5. washwashed with THF
  6. concentrationThe filtrate was concentrated
  7. customThe crude product was purified by column chromatography
  8. washfor elution

Quellen und Nachweise

ORD-Eintrag
ord-060b8dc5b83843be9481efd86d3fe63c
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703768B2

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