Carbon Dioxide → 2-(4-Amino-6-tert-butylpyridin-3-yl)-6-tert-butyl-3H-imidazo[4,5-c]pyridine

HRID 921041Notes

Reaction equation

HRID 921041 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[N:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH2:10].C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O.[CH2:24](O)[CH3:25]>O>[NH2:10][C:9]1[CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:6]=[CH:5][C:24]=1[C:25]1[NH:3][C:4]2[CH:5]=[N:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=2[N:10]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 702EthanolHCID 10340Sodium CarbonateHCID 679950033,4-Diamino-6-tert-butylpyridine dihydrochloride

Product 1

HCID 679963832-(4-Amino-6-tert-butylpyridin-3-yl)-6-tert-butyl-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Procedure analogous to 18) S47, using 71.4 g (300 mmol) of 3,4-diamino-6-tert-butylpyridine dihydrochloride (S50) instead of 90.5 g (500 mmol) of o-phenylenediamine dihydrochloride. After cooling, the deep-blue melt is dissolved in a mixture of 150 ml of ethanol and 300 ml of water at elevated temperature, and a solution of 25 g of sodium carbonate in 100 ml of water is then added dropwise with vigorous stirring (note: foaming, evolution of carbon dioxide). When the addition is complete, the mixture is stirred for a further 30 min., the brown solid is then filtered off with suction, washed three times with 100 ml of water each time and dried in vacuo. Yield: 40.5 g, 74% of a 1:1 mixture of the product and 2,6-di-tert-butyl-3H-imidazo[4,5-c]pyridine, which is reacted without further purification.

Workup

  1. temperatureAfter cooling
  2. additionWhen the addition
  3. filtrationthe brown solid is then filtered off with suction
  4. washwashed three times with 100 ml of water each time
  5. customdried in vacuo
  6. additionYield: 40.5 g, 74% of a 1:1 mixture of the product and 2,6-di-tert-butyl-3H-imidazo[4,5-c]pyridine, which
  7. customis reacted without further purification

Sources & evidence

ORD record
ord-09227b7a7d624919a428c56838a2d70c
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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