3-Morpholino-5-nitropyridin-4-amine → 5-Morpholinopyridine-3,4-diamine

HRID 1397094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397094
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[N:9][CH:10]=[C:11]([N+:14]([O-])=O)[C:12]=2[NH2:13])[CH2:3][CH2:2]1>CO.[Pd]>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:12]([NH2:13])=[C:11]([NH2:14])[CH:10]=[N:9][CH:8]=2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 1

HCID 583779133-Morpholino-5-nitropyridin-4-amine

Produkt 1

HCID 583779865-Morpholinopyridine-3,4-diamineAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 3-morpholino-5-nitropyridin-4-amine (LIII) (1 eq) in MeOH was added 10% Pd/C. The solution was purged with hydrogen and stirred overnight at r.t. under hydrogen. The suspension was filtered through Celite and concentrated under vacuum to produce 5-morpholinopyridine-3,4-diamine (LIV) as a purple solid (37% yield). 1H NMR (DMSO-d6, 400 MHz,): δ 3.09-3.11 (m, 4H), 3.64-3.66 (m, 4H), 3.92 (s, 2H), 5.23 (s, 2H), 6.94 (s, 1H), 7.33 (s, 1H). ESIMS found C9H14N4O m/z 195 (M+H).

Aufarbeitung

  1. customThe solution was purged with hydrogen
  2. filtrationThe suspension was filtered through Celite
  3. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-71a60576ac7a4e9aab1a266a7ab44a69
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901150B2

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