3-Pyridinemethanamine → 6-chloro-N-(pyridin-3-ylmethyl)pyrazin-2-amine

HRID 1244396Notes

Reaction equation

HRID 1244396 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1>C1(C)C(C)=CC=CC=1>[Cl:8][C:4]1[N:3]=[C:2]([NH:16][CH2:15][C:11]2[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=2)[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 785042,6-Dichloropyrazine

Product 1

HCID 219193566-chloro-N-(pyridin-3-ylmethyl)pyrazin-2-amineYield 93%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture 2,6-dichloropyrazine (0.671 mmol) and 3-picolylamine (2.014 mmol) in xylene (25 ml) was refluxed overnight. The residue obtained after evaporation of the solvent was suspended between CH2Cl2 (100 ml) and water (100 ml). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×50 ml). The combined organic extracts were washed with brine (1×100 ml), dried (Na2SO4) and the solvent removed in vacuo. The residue was then purified by column chromatography eluting with a hexane:ethyl acetate gradient mixture to afford the desired product (93%).

Workup

  1. customThe residue obtained
  2. customafter evaporation of the solvent
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×50 ml)
  5. washThe combined organic extracts were washed with brine (1×100 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed in vacuo
  8. customThe residue was then purified by column chromatography
  9. washeluting with a hexane

Sources & evidence

ORD record
ord-ebc62879260449368e8b48b95782d75c
Source dataset
uspto-grants-2006_10
Patent number
US07122550B2

Reaction notes

Loading…