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Water → 5-Ethyl-N-methyl-2-pyridinamine

HRID 63654
Notes
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Reaction equation

HRID 63654 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1)[CH3:2].[Li][CH2:11]CCC.CI.O>C1COCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH3:11])=[N:7][CH:8]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 98127775-Ethylpyridin-2-amineHCID 178418339Butyllithium

Product 1

HCID 235371375-Ethyl-N-methyl-2-pyridinamineYield 9.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Conditions

Temperature
-78 °C

Procedure

A solution of 5-ethylpyridin-2-amine (330 mg, 2.70 mmol) in THF (10 mL) was cooled to −78° C. and n-BuLi (1.2 mL, 3.0 mmol) was added. The reaction stirred at −78° C. for 30 min, and then MeI (423 mg, 2.97 mmol) was added. The reaction was stirred for 2 h while warming to r.t. Water (10 mL) was added, and the solution was extracted with EtOAc (20 mL). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (PE:EtOAc=5:1) to give 35 mg (9%) of the title compound as a yellow oil. [M+H] Calc'd for C8H12N2, 137. Found, 137.

Workup

  1. stirringThe reaction was stirred for 2 h
  2. temperaturewhile warming to r.t
  3. extractionthe solution was extracted with EtOAc (20 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-335435bb2e8c4f4d881559413a5cdb70
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447046B2

Reaction notes

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