2-Amino-3-methylpyridine → HCID 178470327, compound

HRID 1906001Notes

Reaction equation

HRID 1906001 reaction equation
Br[CH2:2][C:3]([C:5]1[S:9][C:8]([OH:10])=[N:7][C:6]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=O.[NH2:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=1>COCCOC>[CH2:14]([O:13][C:11]([C:6]1[N:7]=[C:8]([OH:10])[S:9][C:5]=1[C:3]1[N:16]=[C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]2[CH:2]=1)=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 178470329HCID 178470329, compound

Product 1

HCID 178470327HCID 178470327, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of ethyl 5-(2-bromoacetyl)-2-hydroxy-4-thiazolecarboxylate (2.94 g) and 2-amino-3-methylpyridine (3.24 g) in 1,2-dimethoxyethane (100 ml) was refluxed for 1.5 hours. The reaction mixture was evaporated in vacuo. To the residue was added a mixture of ethyl acetate and water, and the resulting mixture was acidified to pH 0.8 with 10% hydrochloric acid. The separated aqueous layer was adjusted to pH 7.5 with 20% potassium carbonate and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated and diethyl ether and recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 2-(4-ethoxycarbonyl-2-hydroxy-5-thiazolyl)-8-methylimidazo[1,2-a]pyridine (1.76 g). mp 240°-242° C. (dec.)

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionTo the residue was added
  3. additiona mixture of ethyl acetate and water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was triturated
  9. customdiethyl ether and recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-58edf46ba2594193aed0ecae27f3fe25
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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