Aluminium lithium hydride → (6-(Methoxy(methyl)amino)-4-(methylamino)pyridin-3-yl)methanol

HRID 599327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599327
[CH3:1][O:2][N:3]([CH3:17])[C:4]1[CH:14]=[C:13]([NH:15][CH3:16])[C:7]([C:8](OCC)=[O:9])=[CH:6][N:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][N:3]([CH3:17])[C:4]1[N:5]=[CH:6][C:7]([CH2:8][OH:9])=[C:13]([NH:15][CH3:16])[CH:14]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 86629461Ethyl 6-(methoxy(methyl)amino)-4-(methylamino)nicotinate

Produkt 1

HCID 86629462(6-(Methoxy(methyl)amino)-4-(methylamino)pyridin-3-yl)methanolAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 6-(methoxy(methyl)amino)-4-(methylamino)nicotinate (6 g, 25 mmol) in THF (60 mL) at 0° C. was added LiAlH4 (1.9 g, 50.2 mmol) in portions under N2 atmosphere. After 20 min, the reaction was quenched by addition of water followed by aqueous 2N NaOH. The resultant suspension was filtered and the filtrate was concentrated in vacuo to afford (6-(methoxy(methyl)amino)-4-(methylamino)pyridin-3-yl)methanol (3.8 g, 77.6% yield), which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 7.61 (s, 1 H), 6.08 (s, 1 H), 5.86 (m, 1 H), 4.88 (t, J=5.2 Hz, 1 H), 4.30 (d, J=5.2 Hz, 2 H), 3.64 (s, 3 H), 3.04 (s, 3 H), 2.73 (d, J=4.8 Hz, 3 H); MS (ESI) m/z: 198.2 (M+H+).

Aufarbeitung

  1. customthe reaction was quenched by addition of water
  2. filtrationThe resultant suspension was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b2a6801564cd4a7ab447414623b97176
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897762B2

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