Potassium Carbonate → 4-Chloro-6-ethylpyridin-2-amine

HRID 69972Notes

Reaction equation

HRID 69972 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([NH2:9])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Zn](CC)[CH2:17][CH3:18]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:17][CH3:18])[N:5]=[C:4]([NH2:9])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 53166492-Amino-4,6-dichloropyridineHCID 178418750HCID 178418750, compound

Product 1

HCID 690433694-Chloro-6-ethylpyridin-2-amineYield 33%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4,6-dichloropyridin-2-amine (1.0 equiv.) in THF (0.1M) was added Pd(dppf)Cl2-DCM (0.1M), K2CO3 (3.0 equiv.), and Et2Zn (1.2 equiv.). The reaction was heated to 70° C. for 18 hrs. Upon cooling to room temperature, NH4Cl(sat.) was added, the mixture was extracted with EtOAc, dried with Na2SO4, and concentrated. The crude material was purified via SiO2 column chromatography eluting with DCM/MeOH (2%) to yield 4-chloro-6-ethylpyridin-2-amine in 33% yield. LCMS (m/z): 157.1 (MH+).

Workup

  1. temperatureUpon cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe crude material was purified via SiO2 column chromatography
  6. washeluting with DCM/MeOH (2%)

Sources & evidence

ORD record
ord-a0266f5e87fd437b9ef457e73767b91a
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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