Methyl iodide → HCID 67164342, compound

HRID 552776Notes

Reaction equation

HRID 552776 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([OH:15])[CH2:13][C@H:12]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:35]I>C1COCC1>[Si:1]([O:8][CH2:9][C@H:10]1[O:11][C@@H:12]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:13][C@@H:14]1[O:15][CH3:35])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67165367HCID 67165367, compound

Product 1

HCID 67164342HCID 67164342, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,3S,5R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-[6-(2-phenylethyl)-9H-purin-9-yl]tetrahydrofuran-3-ol (98 mg, 0.22 mmol) in THF (1.5 mL) at 0° C. was added NaH (60% in oil, 13 mg, 0.33 mmol) and the suspension stirred for 10 minutes. MeI (26 μL, 0.26 mmol) was added dropwise and the reaction was warmed to room temperature. After one hour the reaction was quenched with saturated aq NH4Cl, partitioned between brine and EtOAc, separated, and the aq layer was extracted with EtOAc (5×). The combined organics were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography (20 to 50% EtOAc/hexanes) to give the title compound (67 mg, 65%).

Workup

  1. customAfter one hour the reaction was quenched with saturated aq NH4Cl
  2. custompartitioned between brine and EtOAc
  3. customseparated
  4. extractionthe aq layer was extracted with EtOAc (5×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (20 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d970652d6e6442a48f3f4ecc8569d14e
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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