Tetrabutylammonium Fluoride → HCID 178508640, compound

HRID 1727333Notes

Reaction equation

HRID 1727333 reaction equation
C([CH:4]([C@@H:14]1[CH2:17][C@H:16]([N:18]2[CH:26]=[N:25][C:24]3[C:19]2=[N:20][CH:21]=[N:22][C:23]=3[NH2:27])[CH2:15]1)[C:5](C(C)C)(C(C)C)[O:6][SiH3])(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][CH2:5][CH2:4][C@@H:14]1[CH2:17][C@H:16]([N:18]2[CH:26]=[N:25][C:24]3[C:19]2=[N:20][CH:21]=[N:22][C:23]=3[NH2:27])[CH2:15]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178445819HCID 178445819, compound

Product 1

HCID 178508640HCID 178508640, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 25 mL flask with 9-[cis-3-(triisopropyl-siloxyethyl)cyclobutyl]adenine (0.07 g, 0.18 mmol) inside, dry THF 1.5 mL was added to give a totally clear light-yellow solution. This was treated with TBAF (1.0 M in THF, 0.36 mL, 0.36 mmol) at room temperature. After 1 hr, the solvent was removed and the crude product was directly applied to the silica gel flash chromatography (CH2Cl2 to CH2Cl2: MeOH=5:1) to give 0.04 g (90%) the desired product. MS (FAB): expected for C11H15N5O (M+H)+ 234.27. Found 234.13482.

Workup

  1. customto give a totally clear light-yellow solution
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-f778e793475b4f079ce1770092c58807
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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