2-Amino-3-methylpyridine → 1263089-45-7

HRID 1023277Notes

Reaction equation

HRID 1023277 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[S:11][C:12]([CH2:15]Cl)=[CH:13][N:14]=1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[Cl:9][C:10]1[S:11][C:12]([CH2:15][NH:1][C:2]2[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 153472-Amino-3-methylpyridineHCID 516892Sodium BicarbonateHCID 27631792-Chloro-5-chloromethylthiazole

Product 1

HCID 601517451263089-45-7Yield 83.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-amino-3-methylpyridine (2.16 g, 20 mmol) and 2-chloro-5-(chloromethyl)thiazole (1.68 g, 10 mmol) in N-methylpyrrolidinone (10 mL) was heated at 180° C. in a microwave reactor for 10 min. The cooled reaction mixture was poured into a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium bicarbonate solution, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluted with 10% ethyl acetate in hexanes to provide the title compound as an oil (2.0 g).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel
  8. washeluted with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-418114a5c24a4d0180b63c6d1545d100
Source dataset
uspto-grants-2014_05
Patent number
US08722690B2

Reaction notes

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