Trimethylsilyl triflate → HCID 57867376, compound

HRID 1516258Notes

Reaction equation

HRID 1516258 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.N12CCCN=C1CCCCC2.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[C:34]([O:42][CH2:43][C@@H:44]1[C@@:48]([O:50][C:51](=[O:53])[CH3:52])([CH3:49])[C@:47]([F:55])([CH3:54])[CH:46](OC(=O)C)[O:45]1)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(#N)C>[C:34]([O:42][CH2:43][C@@H:44]1[C@@:48]([O:50][C:51](=[O:53])[CH3:52])([CH3:49])[C@:47]([F:55])([CH3:54])[CH:46]([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[Cl:1])[O:45]1)(=[O:41])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53592776-ChloropurineHCID 68981036HCID 68981036, compound

Product 1

HCID 57867376HCID 57867376, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of 6-chloropurine (about 0.87 g, 5.7 mmol) in acetonitrile (about 20 ml) was added 1,8-Diazabicyclo[5.4.0]undec-7-ene (about 1.7 ml, 11.4 mmol) and Trimethylsilyl trifluoromethanesulfonate (about 2.76 ml, 15.2 mmol) at about 0° C., stirred for about 15 minutes then ((2R,3S,4R)-3,5-diacetoxy-4-fluoro-3,4-dimethyl-tetrahydrofuran-2-yl)methyl benzoate (about 1.4 g, 3.8 mmol) dissolved in Acetonitrile (about 20 ml) was added and reaction continued stirring at about 65° C. for about 8 hours. Completion of reaction monitored by thin-layer chromatography and quenched with saturated sodium bicarbonate. Aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with saturated sodium bicarbonate solution, brine and dried over sodium sulphate. Concentration under reduced pressure and purification by silica gel column chromatography using 20% ethyl acetate: hexane as eluent furnished title compounds Isomer A and B (0.7 g) as a colorless liquid. Yield: 57%;

Workup

  1. additionwas added
  2. customreaction
  3. stirringcontinued stirring at about 65° C. for about 8 hours
  4. customCompletion of reaction
  5. customquenched with saturated sodium bicarbonate
  6. extractionAqueous layer was extracted with ethyl acetate
  7. washthe combined organic layers were washed with saturated sodium bicarbonate solution, brine
  8. dry with materialdried over sodium sulphate
  9. concentrationConcentration
  10. customunder reduced pressure and purification by silica gel column chromatography
  11. customhexane as eluent furnished title compounds Isomer A and B (0.7 g) as a colorless liquid

Sources & evidence

ORD record
ord-f7be0f8428764c54b4482b39229d2698
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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