2,3-Diaminopyridine → HCID 14499805, compound

HRID 2073793Notes

Reaction equation

HRID 2073793 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.S(O[CH:14]([CH2:18][C:19]#[CH:20])[C:15](=O)[CH3:16])(C)(=O)=O>CO>[NH2:8][C:7]1[C:2]2[N:3]([C:14]([CH2:18][C:19]#[CH:20])=[C:15]([CH3:16])[N:1]=2)[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 99562,3-DiaminopyridineHCID 143683463-Mesyloxy-5-hexyn-2-one

Product 1

HCID 14499805HCID 14499805, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,3-diaminopyridine (62.8 g) and 3-mesyloxy-5-hexyn-2-one (109.5 g) in methanol (126 ml) was refluxed for 20 hours. After methanol was evaporated in vacuo, sodium bicarbonate aqueous solution was added to the residue and then the mixture was extracted with ethyl acetate, washed with water and sodium chloride aqueous solution, and evaporated in vacuo. The resultant residue was subjected to column chromatography on silica gel (310 g) and eluted with a mixture of methylene chloride and acetonitrile. The eluates containing the object compound were combined and evaporated in vacuo. The residue was suspended in diethyl ether and the resultant precipitates were collected by filtration to give 8-amino-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (18.42 g).

Workup

  1. temperaturewas refluxed for 20 hours
  2. customAfter methanol was evaporated in vacuo, sodium bicarbonate aqueous solution
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water and sodium chloride aqueous solution
  6. customevaporated in vacuo
  7. washeluted with a mixture of methylene chloride and acetonitrile
  8. additionThe eluates containing the object compound
  9. customevaporated in vacuo
  10. customthe resultant precipitates
  11. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-1da87bd06eb541a8b8577f5e8c67e128
Source dataset
uspto-grants-1990_04
Patent number
US04920129

Reaction notes

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