Hydrofluoric Acid → HCID 67165700, compound

HRID 552769Notes

Reaction equation

HRID 552769 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[C@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]2[C@H:12]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][CH:23]=[N:24][C:25]=3[CH2:29][CH2:30][O:31][CH3:32])[O:11]1)(C(C)(C)C)(C)C.F>C1COCC1.N1C=CC=CC=1.N1C=CC=CC=1>[CH3:32][O:31][CH2:30][CH2:29][C:25]1[N:24]=[CH:23][N:22]=[C:21]2[C:26]=1[N:27]=[CH:28][N:20]2[C@H:12]1[C@@H:13]2[O:17][C:16]([CH3:18])([CH3:19])[O:15][C@@H:14]2[C@@H:10]([CH2:9][OH:8])[O:11]1

Participants

5

Reactant 2

HCID 14917Hydrofluoric AcidHCID 671641629-[(3aR,4R,6R,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-(2-methoxyethyl)-9H-purine

Product 1

HCID 67165700HCID 67165700, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

To a solution of 9-[(3aR,4R,6R,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-(2-methoxyethyl)-9H-purine (70 mg, 0.15 mmol) in THF/pyridine (1.5 mL, 1:1) was added hydrofluoric acid in pyridine (15 drops). The reaction was stirred overnight, quenched with saturated aq NaHCO3, extracted with EtOAc, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0 to 50% DCM/EtOAc to furnish 37 mg (70%) of the title compound.

Workup

  1. customquenched with saturated aq NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (0 to 50% DCM/EtOAc

Sources & evidence

ORD record
ord-bb5911bed4f149e0b039f582237eb9f4
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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