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

HRID 599327Notes

Reaction equation

HRID 599327 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 86629462(6-(Methoxy(methyl)amino)-4-(methylamino)pyridin-3-yl)methanolYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-b2a6801564cd4a7ab447414623b97176
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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