HCID 67164829, compound → HCID 67164798, compound

HRID 552693Notes

Reaction equation

HRID 552693 reaction equation
[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C@@H:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21]2)[O:7][C@@H:6]1[CH2:29][O:30][Si](C(C)(C)C)(C)C)(=[O:3])[CH3:2]>N1C=CC=CC=1.O1CCCC1.F.N1C=CC=CC=1>[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C@@H:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21]2)[O:7][C@@H:6]1[CH2:29][OH:30])(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 67164829HCID 67164829, compound

Product 1

HCID 67164798HCID 67164798, compoundYield 91.3%

Reagents, catalysts & solvents 3

HCID 14917Hydrofluoric AcidCatalystHCID 1049PyridineSolventHCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

To a solution of (2R,3S,5R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-{6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-9H-purin-9-yl}tetrahydrofuran-3-yl acetate (440 mg, 0.84 mmol) in pyridine/tetrahydrofuran (1:1, 3.4 mL) was added approximately 20 drops of hydrofluoric acid in pyridine (2.0 M). After stirring for 17 h, the reaction was quenched with saturated aqueous NaHCO3 and extracted with dichloromethane. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification via flash chromatography (40 to 100% EtOAc/hexanes) afforded 314 mg (91%) of the title compound.

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification via flash chromatography (40 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-117ff84760e940dab01f45b514d5c692
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

Loading…