TBAF tetrahydrofuran → (6-(Thiazol-2-ylamino)pyridin-2-yl)methanol

HRID 1725469Notes

Reaction equation

HRID 1725469 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:15]=[C:14]([NH:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:13]=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>O1CCCC1.C(OCC)(=O)C>[S:18]1[CH:19]=[CH:20][N:21]=[C:17]1[NH:16][C:14]1[N:15]=[C:10]([CH2:9][OH:8])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 57562580HCID 57562580, compound

Product 1

HCID 57562655(6-(Thiazol-2-ylamino)pyridin-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6.48g of 6-(((tert-butyl(dimethyl)silyl)oxy)methyl)-N-thiazol-2-ylpyridin-2-amine was dissolved in 100 ml of tetrahydrofuran. Under cooling with ice, a tetrabutylammonium fluoride-tetrahydrofuran solution (1.0 M, 20.2 ml) was added followed by stirring at room temperature for 1 hour. The reaction solution was diluted with ethyl acetate and then washed with phosphate buffer (pH 6.8). The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated to give the title compound.

Workup

  1. temperatureUnder cooling with ice
  2. washwashed with phosphate buffer (pH 6.8)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-528ee22ff48840e2a15013be0df38618
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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