Aluminium lithium hydride → HCID 86629465, compound

HRID 599334Notes

Reaction equation

HRID 599334 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([NH:10][C:11]1[C:16]([C:17](OCC)=[O:18])=[CH:15][N:14]=[C:13]([N:22]([O:24][CH3:25])[CH3:23])[CH:12]=1)([CH3:9])[CH3:8]>C1COCC1>[CH:7]([NH:10][C:11]1[CH:12]=[C:13]([N:22]([O:24][CH3:25])[CH3:23])[N:14]=[CH:15][C:16]=1[CH2:17][OH:18])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86629463Ethyl 6-(methoxymethylamino)-4-[(1-methylethyl)amino]-3-pyridinecarboxylate

Product 1

HCID 86629465HCID 86629465, compoundYield 107.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (0.9 g, 24.0 mmol) was added in portions to a solution of ethyl 4-(isopropylamino)-6-(methoxy(methyl)amino)nicotinate (3.2 g, 12.0 mmol) in THF (60 mL) at 0° C. and the resultant reaction mixture was stirred at RT for 30 min. The reaction was quenched by the addition of water (1 mL) and aqueous 2N NaOH (1 mL). The resulting precipitates were removed by filtration and the filtrate was concentrated to afford (4-(isopropylamino)-6-(methoxy(methyl)amino)pyridine-3-yl)methanol (2.9 g, >100% yield), which was used without further purification. 1HNMR (400 MHz, DMSO-d6): δ 7.62 (s, 1 H), 6.16 (s, 1 H), 5.44 (d, J=7.2 Hz, 1 H), 5.02 (bs, 1 H), 4.33 (s, 2 H), 3.69-3.61 (m, 4 H), 3.06 (s, 3 H), 1.18 (d, J=6.4 Hz, 6 H).

Workup

  1. customthe resultant reaction mixture
  2. customThe reaction was quenched by the addition of water (1 mL) and aqueous 2N NaOH (1 mL)
  3. customThe resulting precipitates
  4. customwere removed by filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4208e7356dc549d09af96b1ddb6b3f3d
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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