Dimethylformamide → HCID 86648286, compound

HRID 1889188Notes

Reaction equation

HRID 1889188 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6](O)[N:5]=2.[F-].[Cs+].[CH2:14](I)[CH3:15].CN(C)C=[O:20]>O>[CH2:14]([O:20][NH:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][N:5]=2)[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 25953Cesium fluorideHCID 178508197HCID 178508197, compound

Product 1

HCID 86648286HCID 86648286, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-Amino-thiazolo[5,4-b]pyridin-5-ol (4.7 g, 28.1 mmol) in Dimethylformamide (50 ml) was added cesium fluoride (12.8 g, 84.4 mmol) under argon atmosphere. Ethyl iodide ((2.7 ml, 33.7 mmol) was added in drop wise manner at room temperature and stirred overnight. Completion of reaction was confirmed by TLC, reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate (100 ml×3),combined organic extracts were washed with water and brine (100 ml each) dried over Na2SO4, filtered and concentrated under vaccum to afford ethoxy-thiazolo[5,4-b]pyridin-2-ylamine (2.1 g).

Workup

  1. customCompletion of reaction
  2. customwas confirmed by TLC, reaction mixture
  3. extractionextracted with ethyl acetate (100 ml×3),combined organic extracts
  4. washwere washed with water and brine (100 ml each)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vaccum

Sources & evidence

ORD record
ord-73c9d9b33e384dda97d4f4b618266722
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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