HCID 86607298, compound → HCID 86607329, compound

HRID 552755Notes

Reaction equation

HRID 552755 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:21][C@H:20]2[C@@H:13]([O:14][Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)[O:18][CH2:19]2)[C@@H:12]1[O:34][CH3:35]>C1COCC1.N1C=CC=CC=1.F.N1C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:21][C@H:20]([CH2:19][OH:18])[C@@H:13]([OH:14])[C@@H:12]1[O:34][CH3:35]

Participants

6

Reactant 1

HCID 86607298HCID 86607298, compound

Product 1

HCID 86607329HCID 86607329, compoundYield 95.2%

Reagents, catalysts & solvents 4

HCID 14917Hydrofluoric AcidCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolventHCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-9-[(6aR,8R,9S,9aR)-2,2,4,4-tetraisopropyl-9-methoxytetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-9H-purine (1.31 g, 2.41 mmol) in THF/pyridine (12 mL, 1:1) was added approximately 20 drops of hydrofluoric acid in pyridine. This solution was stirred at r.t. overnight. The reaction was diluted with EtOAc (10 mL) and quenched with saturated aq NaHCO3. The aq layer was extracted with EtOAc (3×40 mL) and the combined organics were dried (Na2SO4), filtered, and concentrated. The crude material was purified by flash chromatography (0 to 10% MeOH/DCM) to afford the title compound (0.690 g, 74%).

Workup

  1. customquenched with saturated aq NaHCO3
  2. extractionThe aq layer was extracted with EtOAc (3×40 mL)
  3. dry with materialthe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (0 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-ae290d9c4ccc44ac9bd955fc5dc43218
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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