Cesium carbonate → HCID 89536594, compound

HRID 2171241Notes

Reaction equation

HRID 2171241 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].C[NH:13][C@@H:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]1[NH:20]C.Br[C:23]1[CH:24]=[C:25]([NH2:30])[CH:26]=[N:27][C:28]=1[CH3:29]>[Cu](I)I.O.CC(N(C)C)=O>[CH3:19][C:18]1[N:13]=[CH:14][C:15]([NH2:20])=[CH:16][C:17]=1[N:2]1[N:3]=[CH:4][CH:5]=[N:1]1.[CH3:29][C:28]1[N:27]=[CH:26][C:25]([NH2:30])=[CH:24][C:23]=1[N:1]1[CH:5]=[CH:4][N:3]=[N:2]1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 184588965-Bromo-6-methylpyridin-3-amineHCID 178418936HCID 178418936, compound

Product 2

HCID 89536594HCID 89536594, compoundHCID 89536837HCID 89536837, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

1,2,3-Triazole (45 mg), cesium carbonate (260 mg), trans-N,N′-dimethylcyclohexan-1,2-diamine (76 mg), and copper iodide (50 mg) were added to a DMAc (2 ml) solution containing 5-bromo-6-methylpyridin-3-amine (100 mg) in a nitrogen atmosphere, followed by stirring in a sealed tube at 110° C. for 8 hours. The reaction solution was adjusted to room temperature and water was added to the reaction solution, followed by extraction with ethyl acetate and washing with saturated saline. The organic layers were dried over anhydrous sodium sulfate. Next, the solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 20:1). A white solid of 6-methyl-5-(2H-1,2,3-triazol-2-yl)pyridin-3-amine (12.8 mg) and brown oily matter of 6-methyl-5-(1H-1,2,3-triazol-1-yl)pyridin-3-amine (6.7 mg) were thus obtained.

Workup

  1. customwas adjusted to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing with saturated saline
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  5. distillationNext, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 20:1)

Sources & evidence

ORD record
ord-b4eb451a27c546479d76d6a86b6bf715
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

Loading…