2-Aminopyridine → HCID 10536778, compound

HRID 2097327Notes

Reaction equation

HRID 2097327 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([O:10][C:11]1[C:12](=O)[C:13](=[O:18])[C:14]=1[O:15]CC)[CH3:9]>CCO>[CH2:8]([O:10][C:11]1[C:14](=[O:15])[C:13](=[O:18])[C:12]=1[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:9]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 123228Diethyl squarate

Product 1

HCID 10536778HCID 10536778, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Aminopyridine (630 mg, 6.7 mmol) was added to a solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (1.0 mL, 6.7 mmol) in EtOH (10 mL). The mixture was heated to reflux for 2.5 h, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (800 mL hexanes/EtOAc 3:1, 1.5 L hexanes/EtOAc 1:1) to give 431 mg (29%) of the title compound as a yellow powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2.5 h
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (800 mL hexanes/EtOAc 3:1, 1.5 L hexanes/EtOAc 1:1)

Sources & evidence

ORD record
ord-a1eec3a3ecfc4228bf6ce96b0e58be0d
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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