Tetrabutylammonium Fluoride → HCID 90403565, compound

HRID 2200608Notes

Reaction equation

HRID 2200608 reaction equation
[OH:1][CH:2]([CH3:37])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[N:11](COCC[Si](C)(C)C)[C:10]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:34])([F:33])[F:32])[CH:25]=3)=[N:9][C:8]=2[N:7]([CH3:35])[C:6]1=[O:36].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[OH:1][CH:2]([CH3:37])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:33])([F:34])[F:32])[CH:25]=3)=[N:9][C:8]=2[N:7]([CH3:35])[C:6]1=[O:36]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90402694HCID 90402694, compound

Product 1

HCID 90403565HCID 90403565, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(3-hydroxybutyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (1.1 g, 2.02 mmol) in THF (5 mL) was added TBAF (5 mL, 1 mmol/L in THF) and the mixture was heated at reflux for 16 h. The mixture was cooled and diluted with ethyl acetate. The organic phase was washed with brine and saturated aqueous ammonium chloride; then it was dried and concentrated to give a crude product which was purified by silica gel chromatography eluting with DCM/methanol (45:1) to give (701 mg, 83.8% yield) as white solid. LCMS retention time 1.372 min; LCMS MH+ 415.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  3. temperatureThe mixture was cooled
  4. washThe organic phase was washed with brine and saturated aqueous ammonium chloride
  5. customthen it was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-40a1862452074fc1b2d5db3c37e63ac4
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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