Potassium Carbonate → 6-chloro-N-methyl-N-(1-methylpropyl)pyrazin-2-amine

HRID 2188658Notes

Reaction equation

HRID 2188658 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH3:9][NH:10][CH:11]([CH2:13][CH3:14])[CH3:12].C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O>O>[Cl:8][C:4]1[N:3]=[C:2]([N:10]([CH3:9])[CH:11]([CH3:12])[CH2:13][CH3:14])[CH:7]=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 785042,6-DichloropyrazineHCID 111026N-Methyl-2-butanamine

Product 1

HCID 616997676-chloro-N-methyl-N-(1-methylpropyl)pyrazin-2-amineYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-dichloropyrazine (1.49 g), N-methylbutan-2-amine (1.31 mL), potassium carbonate (2.07 g) and DMA (10 mL) was stirred at 80° C. for 40 hr. Water (10 mL) was added, and the mixture was extracted with ethyl acetate. The aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient: 5→20% ethyl acetate/hexane) to give the title compound (1.43 g, 72%) as a pale-yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. extractionThe aqueous layer was extracted again with ethyl acetate
  3. washThe combined organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (solvent gradient: 5→20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-78f554e8ad9d4d1aa9fb07ac4b4d5e62
Source dataset
uspto-grants-2012_12
Patent number
US08324201B2

Reaction notes

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