2-Amino-3-methylpyridine → HCID 20145010, compound

HRID 1905995Notes

Reaction equation

HRID 1905995 reaction equation
Br.[NH2:2][C:3]1[S:4][C:5]([C:9](=O)[CH2:10]Br)=[C:6]([CH3:8])[N:7]=1.[NH2:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1>CC(N(C)C)=O>[NH2:2][C:3]1[S:4][C:5]([C:9]2[N:13]=[C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]3[CH:10]=2)=[C:6]([CH3:8])[N:7]=1

Participants

4

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 20145033HCID 20145033, compound

Product 1

HCID 20145010HCID 20145010, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-amino-4-methyl-5-(2-bromoacetyl)thiazole hydrobromide (9.5 g) and 2-amino-3-methylpyridine (9.7 g) in dimethylacetamide (100 ml) was heated at 85° C. to 88° C. for 5 hours and the reaction mixture was evaporated in vacuo. To the residue was added water and the resulting mixture was acidified to pH 0.8 with 10% hydrochloric acid. The acidified solution was treated with charcoal and filtered. The filtrate was washed with ethyl acetate. The aqueous solution was adjusted to pH 9.0 with aqueous potassium carbonate and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 2-(2-amino-4-methyl-5-thiazolyl)-8-methylimidazo[1,2-a]pyridine (1.6 g). mp 226° C. (dec.)

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. additionTo the residue was added water
  3. additionThe acidified solution was treated with charcoal
  4. filtrationfiltered
  5. washThe filtrate was washed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extract was dried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-d556ae71631446d4adc483c30e4fbf05
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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