Water → 6-chloro-N-cyclobutylpyrazin-2-amine

HRID 518065Notes

Reaction equation

HRID 518065 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH:9]1([NH2:13])[CH2:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[Cl:8][C:4]1[N:3]=[C:2]([NH:13][CH:9]2[CH2:12][CH2:11][CH2:10]2)[CH:7]=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 75645CyclobutylamineHCID 785042,6-Dichloropyrazine

Product 1

HCID 624152146-chloro-N-cyclobutylpyrazin-2-amineYield 80%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2,6-dichloropyrazine (4.47 g), cyclobutanamine (3.8 mL) and potassium carbonate (6.20 g) in DMA (30 mL) was stirred at 80° C. for 14 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient: 5-15% ethyl acetate/hexane) to give the title compound (4.42 g, 80%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent gradient: 5-15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e07215a352aa4cd490c83546f5356868
Source dataset
uspto-grants-2015_08
Patent number
US09115139B2

Reaction notes

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