Tetrabutylammonium Fluoride → HCID 137108749, compound

HRID 60763Notes

Reaction equation

HRID 60763 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:28])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@H:12]3[C@H:16]([C:17]#[N:18])[CH2:15][C@@H:14]([CH2:19][O:20][Si](C(C)(C)C)(C)C)[O:13]3)[C:6]=2[N:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:1][C:2]1[NH:3][C:4](=[O:28])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@H:12]3[C@H:16]([C:17]#[N:18])[CH2:15][C@@H:14]([CH2:19][OH:20])[O:13]3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 137190222HCID 137190222, compound2×

Product 1

HCID 137108749HCID 137108749, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (2R,3S,5S)-2-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]tetrahydrofuran-3-carbonitrile (compound 38h, crude, 100 mg) in THF (5 mL) was added TBAF solution (1M in THF, 6 mL, 6 mmol) at 0° C. After being stirred at room temperature for 4 hours, the reaction solution was washed with saturated NH4Cl solution, dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative HPLC to afford 9 mg of (2R,3S,5S)-2-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)tetrahydrofuran-3-carbonitrile (Example 38) as a white solid.

Workup

  1. washthe reaction solution was washed with saturated NH4Cl solution
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a450c31b3b184211be1a606f1c90b7ce
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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