Diethyl Ether → 2-t-Butylthio-3-(aminomethyl)-5-ethyl-6-methylpyridine

HRID 1033013Notes

Reaction equation

HRID 1033013 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([S:11][C:12]1[C:17]([C:18]#[N:19])=[CH:16][C:15]([CH2:20][CH3:21])=[CH:14][N:13]=1)([CH3:10])([CH3:9])[CH3:8].[CH2:22](OCC)C>>[C:7]([S:11][C:12]1[C:17]([CH2:18][NH2:19])=[CH:16][C:15]([CH2:20][CH3:21])=[C:14]([CH3:22])[N:13]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 190862522-t-Butylthio-3-cyano-5-ethylpyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 190862502-t-Butylthio-3-(aminomethyl)-5-ethyl-6-methylpyridine

Procedure

To a suspension of lithium aluminum hydride (54 mg, 1.42 mmol) in diethyl ether (10 mL), under a nitrogen atmosphere, was added dropwise a solution of 2-t-butylthio-3-cyano-5-ethylpyridine (222 mg, 0.95 mmol) in diethyl ether (6 mL). After stirring for 3.5 hours at room temperature, the reaction was quenched with saturated aqueous sodium sulfate and the ether layer dried (Na2SO4), filtered and evaporated to give 219 mg (96%) of crude oily product.

Workup

  1. customthe reaction was quenched with saturated aqueous sodium sulfate
  2. dry with materialthe ether layer dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give 219 mg (96%) of crude oily product

Sources & evidence

ORD record
ord-b2a3d48d4e524de58306e7fc8e5c2a54
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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