Ethyl Acetate → 2-t-Butylamino-3-fluoro-5-methyl-6-(1,1,3,3-tetramethylbutylamino)pyridine

HRID 368467Notes

Reaction equation

HRID 368467 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([NH:11][C:12]1[C:21]([F:22])=[CH:20][C:15]([C:16](OC)=O)=[C:14]([NH:23][C:24]([CH3:31])([CH3:30])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[N:13]=1)([CH3:10])([CH3:9])[CH3:8].C(OCC)(=O)C>O1CCCC1.O.C(O)C>[C:7]([NH:11][C:12]1[C:21]([F:22])=[CH:20][C:15]([CH3:16])=[C:14]([NH:23][C:24]([CH3:31])([CH3:30])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[N:13]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22121205Methyl 6-t-butylamino-5-fluoro-2-(1,1,3,3-tetramethylbutylamino)nicotinate

Product 1

HCID 177787592-t-Butylamino-3-fluoro-5-methyl-6-(1,1,3,3-tetramethylbutylamino)pyridineYield 68.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To 20 ml of tetrahydrofran was dispersed 850 mg of lithium aluminum hydride. The dispersion was water cooled and stirred simultaneously with the dropwise addition of 2.80 g of methyl 6-t-butylamino-5-fluoro-2-(1,1,3,3-tetramethylbutylamino)nicotinate dissolved in 30 ml of tetrahydrofuran. The reactor was placed in an oil bath of 50° C., and the mixture was stirred for two and half hours. The reactor was then water cooled and 8 ml of ethyl acetate was added dropwise, and the mixture was stirred for 1 hour. 8 ml of ethanol was added dropwise, and the mixture was stirred for 1 hour, then 8 ml of distilled water was added dropwise, and the mixture was stirred overnight. The precipitate was separated by filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography (silica gel, 40 g; eluent: chloroform:n-hexane, 1:1) to obtain 1.67 g of the title compound as a colorless oily residue.

Workup

  1. temperaturecooled
  2. customThe reactor was placed in an oil bath of 50° C.
  3. stirringthe mixture was stirred for 1 hour
  4. stirringthe mixture was stirred for 1 hour
  5. stirringthe mixture was stirred overnight
  6. customThe precipitate was separated by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-245c79573ebb4403ae578d9e68cf8eea
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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