Sodium hydride → HCID 67165036, compound

HRID 552766Notes

Reaction equation

HRID 552766 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].C([O:12][CH2:13][C@@H:14]1[C@@H:21]2[C@@H:17]([O:18][C:19]([CH3:23])([CH3:22])[O:20]2)[C@H:16]([N:24]2[CH:32]=[N:31][C:30]3[C:25]2=[N:26][CH:27]=[N:28][C:29]=3[CH:33]=[CH2:34])[O:15]1)(=O)C.[NH4+].[Cl-]>CS(C)=O>[CH:33]1([C:29]2[N:28]=[CH:27][N:26]=[C:25]3[C:30]=2[N:31]=[CH:32][N:24]3[C@H:16]2[C@@H:17]3[O:18][C:19]([CH3:23])([CH3:22])[O:20][C@@H:21]3[C@@H:14]([CH2:13][OH:12])[O:15]2)[CH2:34][CH2:2]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 67163970HCID 67163970, compound

Product 1

HCID 67165036HCID 67165036, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A suspension of trimethylsulfoxonium iodide (150 mg, 0.68 mmol and NaH (60% in mineral oil, 18 mg, 0.75 mmol) in DMSO (2.00 mL) was stirred for 30 minutes at r.t. [(3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-vinyl-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl acetate (50 mg, 0.0.13 mmol) in DMSO (3 mL) was added slowly and the reaction was stirred at r.t. for 90 minutes. The reaction mixture was treated with saturated aq NH4Cl and extracted with DCM. The combined organics were washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (0 to 50% EtOAc/hexanes) to yield the title compound (15 mg, 33%).

Workup

  1. additionwas added slowly
  2. extractionextracted with DCM
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (0 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1f85df946de146bea186be4fdaa1b3b8
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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