Tetrabutylammonium Fluoride → 4-(Pyrimidin-2-ylmethyl)phenol

HRID 2075223Notes

Reaction equation

HRID 2075223 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:39]=[CH:38][C:30]([CH2:31][C:32]2[N:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C>C1COCC1.O>[N:33]1[CH:34]=[CH:35][CH:36]=[N:37][C:32]=1[CH2:31][C:30]1[CH:38]=[CH:39][C:27]([OH:26])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 584153612-(4-(tert-Butyldimethylsilyloxy)benzyl)pyrimidine

Product 1

HCID 227684204-(Pyrimidin-2-ylmethyl)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.68 mL, 1.68 mmol, 1M in THF) was added to a solution of 2-(4-(tert-butyldimethylsilyloxy)benzyl)pyrimidine (0.50 g, 1.68 mmol) in THF (5 mL) at 0° C. The mixture was stirred for 30 min, diluted with water, and extracted with DCM three times. The combined organic extracts were dried over MgSO4, concentrated in vacuo, and purified by column chromatography to give 4-(pyrimidin-2-ylmethyl)phenol as an oil. MS (ESI) m/z: Calculated: 186.1; Observed: 187.3 (M++1).

Workup

  1. extractionextracted with DCM three times
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-b1c2d85c5e954c369f9b35be8228a736
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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