Ethylenediamine → 2-Amino-6-methoxypyridine

HRID 2297103Notes

Reaction equation

HRID 2297103 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.C(N)C[NH2:12]>>[CH3:9][O:8][C:4]1[N:3]=[C:2]([NH2:12])[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 870092-Chloro-6-methoxypyridine

Product 1

HCID 5800532-Amino-6-methoxypyridine

Procedure

2-Chloro-6-methoxypyridine (5.0 g) was heated with ethylenediamine (30 ml) at 120° C. overnight. The excess ethylenediamine was removed by rotary evaporation. The residue was dissolved in a small volume of 2.5 M aqueous sodium hydroxide and extracted thoroughly with dichloromethane. The combined organic layers were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated in vacuo to give (2-aminoethyl)(6-methoxy(2-pyridyl)amine as an orange syrup. The amine (2.58 g) was treated with benzotriazole carboxamidinium 4-methylbenzenesulfonate (0.86 g) and DIEA (0.45 mmol) in acetonitrile (6 ml) and stirred overnight at room temperature. Trituration with ether gave the guanidine, amino-{2-[(6-methoxy(2-pyridyl))amino]ethyl}carboxamidinium 4-methylbenzenesulfonate, as an oil. The oily guanidine (200 mg) was reacted with 100 mg of resin according to Resin Method C (90° C., overnight) to give the title compound.

Workup

  1. customThe excess ethylenediamine was removed by rotary evaporation
  2. dissolutionThe residue was dissolved in a small volume of 2.5 M aqueous sodium hydroxide
  3. extractionextracted thoroughly with dichloromethane
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36b6284a6553469c8d0c199bef11172b
Source dataset
uspto-grants-2002_12
Patent number
US06489344B1

Reaction notes

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