Tetrabutylammonium Fluoride → 2-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethanol

HRID 1786898Notes

Reaction equation

HRID 1786898 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:19]2[C:18]([Cl:20])=[N:17][CH:16]=[N:15][C:14]=2[CH:13]=[CH:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[Cl:20][C:18]1[C:19]2[N:11]([CH2:10][CH2:9][OH:8])[CH:12]=[CH:13][C:14]=2[N:15]=[CH:16][N:17]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 866157545-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 860848322-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethanolYield 110.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidine (560 mg) in tetrahydrofuran (1.7 mL), was added tetrabutylammonium fluoride (1M tetrahydrofuran solution) (2.69 mL) under ice-cooling, and the mixture was stirred for 4 hrs. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (30 mL×3). The organic layer was washed with saturated brine (30 mL×3) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (silica gel, eluent:ethyl acetate/methanol=10/0→9/1). The object fraction was concentrated under reduced pressure and dried to give the title compound (391 mg) as a white solid.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (30 mL×3)
  3. washThe organic layer was washed with saturated brine (30 mL×3)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe object fraction was concentrated under reduced pressure
  7. customdried

Sources & evidence

ORD record
ord-8ab98b28434e43a4b3f45e237b938e87
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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