2-Amino-3-methoxymethoxypyridine → 8-Hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine

HRID 1762208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1762208
[NH2:1][C:2]1[C:7]([O:8]COC)=[CH:6][CH:5]=[CH:4][N:3]=1.S(O[CH:17]([CH2:21][C:22]#[CH:23])[C:18](=O)[CH3:19])(C)(=O)=O>C(O)C>[OH:8][C:7]1[C:2]2[N:3]([C:17]([CH2:21][C:22]#[CH:23])=[C:18]([CH3:19])[N:1]=2)[CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 143683452-Amino-3-methoxymethoxypyridineHCID 143683463-Mesyloxy-5-hexyn-2-one

Produkt 1

HCID 143683478-Hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridineAusbeute 21,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-amino-3-methoxymethoxypyridine (7.5 g) and 3-mesyloxy-5-hexyn-2-one (10.18 g) in ethanol (150 ml) was refluxed for 46.5 hours and then evaporated in vacuo. To the residue was added 20% sulfuric acid (75 ml) and the mixture was stirred for 5 hours at room temperature. The mixture was made alkaline with sodium bicarbonate and extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (30 g) with chloroform and then a mixture of chloroform and methanol (30:1 to 20:1) as eluents. The eluates were evaporated in vacuo and the residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 8-hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (1.93 g).

Aufarbeitung

  1. customevaporated in vacuo
  2. additionTo the residue was added 20% sulfuric acid (75 ml)
  3. extractionextracted with chloroform
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (30 g) with chloroform
  8. additiona mixture of chloroform and methanol (30:1 to 20:1) as eluents
  9. customThe eluates were evaporated in vacuo
  10. customthe residue was recrystallized from a mixture of ethyl acetate and n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-98c2829e74c34458be64628010fd79be
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04831041

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