2-Amino-5-methylthiazole → Ethyl 2,6-dimethylimidazo[2,1-b]thiazole-5-carboxylate

HRID 560290Notes

Reaction equation

HRID 560290 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][CH:3]=1.[CH2:8]([O:10][C:11](=[O:17])[CH:12](Br)[C:13](=O)[CH3:14])[CH3:9]>CC(C)=O>[CH2:8]([O:10][C:11]([C:12]1[N:4]2[C:5]([S:6][C:2]([CH3:1])=[CH:3]2)=[N:7][C:13]=1[CH3:14])=[O:17])[CH3:9]

Participants

4

Reactant 2

HCID 3517702-Amino-5-methylthiazoleHCID 11206579Ethyl 2-bromo-3-oxobutanoate

Product 1

HCID 15026034Ethyl 2,6-dimethylimidazo[2,1-b]thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-methyl-2-aminothiazole (7.09 mmol) and 2-bromo-3-oxo-butyric acid ethyl ester (8.51 mmol) in acetone (17 mL) is stirred for 16 h at RT and for additional 7 h at reflux. The solvents are removed in vacuo, chloroform and sat aq. NaHCO3 solution are added, the layers are separated and the aq. layer is extracted with chloroform. The combined organic layers are dried over MgSO4 and concentrated in vacuo to give a crude product which is purified by FC (heptane to heptane/EtOAc 6/4). LC-MS: tR=0.80 min; [M+H]+=225.3.

Workup

  1. temperatureat reflux
  2. customThe solvents are removed in vacuo, chloroform
  3. additionare added
  4. customthe layers are separated
  5. extractionthe aq. layer is extracted with chloroform
  6. dry with materialThe combined organic layers are dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94e798d7b7f048bd93d3d1b9dae2b6e4
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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