N,N'-Dimethylethylenediamine → HCID 23339834, compound

HRID 643011Notes

Reaction equation

HRID 643011 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5](Br)=[CH:6][CH:7]=1.[OH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.CNCCNC.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Cu]I.C(O)CCC.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[O:9])=[N:4][CH:3]=1

Participants

9

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 6428116-Bromopyridin-3-amineHCID 178516071HCID 178516071, compound

Product 1

HCID 23339834HCID 23339834, compoundYield 33.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 2631-ButanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-amino-6-bromopyridine (865 mg, 5.00 mmol), 2-hydroxypyridine (475 mg, 5.00 mmol), N,N′-dimethylethylenediamine (0.215 mL, 2.00 mmol) and K2CO3 (1.38 g, 10.0 mmol) in dioxane (8 mL) was degassed with Argon before being charged with CuI (190 mg, 1.00 mmol). The mixture in a sealed tube was heated at 110° C. overnight. After being cooled down, H2O and nBuOH were added. The organic phase was separated, and concentrated in vacuo to give 1-(5-aminopyridin-2-yl)pyridin-2(1H)-one (316 mg).

Workup

  1. customwas degassed with Argon
  2. temperatureAfter being cooled down
  3. customThe organic phase was separated
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b28ddc713e848d9ad8b7a9efde0953e
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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