Trimethyl orthoformate → (1-Ethyl-propyl)-[5-methyl-3-(2,4,6-trimethyl-phenyl)-3H-imidazo[4,5-b]pyridin-7-yl]-amine

HRID 1245748Notes

Reaction equation

HRID 1245748 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].[CH:25](OC)(OC)OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[N:14]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[CH:25]=[N:24][C:8]=12)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 21912187N4-(1-ethyl-propyl)-6-methyl-N2-(2,4,6-trimethyl-phenyl)-pyridine-2,3,4-triamine

Product 1

HCID 21912118(1-Ethyl-propyl)-[5-methyl-3-(2,4,6-trimethyl-phenyl)-3H-imidazo[4,5-b]pyridin-7-yl]-amine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of N4-(1-ethyl-propyl)-6-methyl-N2-(2,4,6-trimethyl-phenyl)-pyridine-2,3,4-triamine (250 mg, 0.77 mmol), trimethyl orthoformate (0.081 g, 0.766 mmol), p-toluenesulfonic acid monohydrate (0.01 g) in benzene was heated at reflux using Dean-Stark apparatus for 24 hours. Benzene was removed and toluene was added and an excess of trimethyl orthoformate (0.084 ml) was added to the reaction mixture. The mixture was heated at reflux overnight. The mixture was quenched with water, sat. NaHCO3, extracted with ethyl acetate. The organic layer was separated, dried (MgSO4) and concentrated to dryness. After purification, the title compound was isolated as a white crystal, mp 78–80° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customfor 24 hours
  4. customBenzene was removed
  5. additiontoluene was added
  6. additionan excess of trimethyl orthoformate (0.084 ml) was added to the reaction mixture
  7. temperatureThe mixture was heated
  8. temperatureat reflux overnight
  9. customThe mixture was quenched with water, sat. NaHCO3
  10. extractionextracted with ethyl acetate
  11. customThe organic layer was separated
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated to dryness
  14. customAfter purification

Sources & evidence

ORD record
ord-458d8c2c1b504d2692d70e98f0f2bcdd
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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