Trimethylsilyl triflate → HCID 67142223, compound

HRID 2212905Notes

Reaction equation

HRID 2212905 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][C:9]([Br:13])=[C:10]([C:11]#[N:12])[C:3]=12.C(O[CH:18]1[O:26][C@H:25]([CH2:27][O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:24]([CH3:37])[C@H:19]1[O:20][C:21](=[O:23])[CH3:22])(=O)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>C(#N)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]2[C:10]([C:11]#[N:12])=[C:9]([Br:13])[N:8]([C@@H:18]3[O:26][C@H:25]([CH2:27][O:28][C:29](=[O:36])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C@@H:24]([CH3:37])[C@H:19]3[O:20][C:21](=[O:23])[CH3:22])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 67143630HCID 67143630, compoundHCID 178509359HCID 178509359, compound

Product 1

HCID 67142223HCID 67142223, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

BSA (0.29 mL, 2.0 mmol) was added into a stirred suspension of 4-amino-6-bromo-5-cyano-1H-pyrrolo[2,3-d]pyrimidine (0.24 g, 1 mmol; prepared according to Nucleic Acid Chemistry, Part IV, Townsend, L. B. and Tipson, R. S.; Ed.; Wiley-Interscience: New York, 1991, pp. 16-17 and Synthetic Commun. 1998, 28, 3835) in dry acetonitrile (10 mL) at room temperature under argon. After 15 min, 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-methyl-D-ribofuranose (J. Med. Chem. (1976), 19, 1265) (0.36 g, 1.0 mmol) was added along with TMSOTf (0.54 g, 3 mmol). The mixture was stirred at room temperature for 5 min and then at 80° C. for 0.5 h. The solution was cooled, diluted with ethyl acetate (50 mL) and poured into ice-cold saturated aqueous NaHCO3 (15 mL). The layers were separated. The organic layer was washed with brine (15 mL), dried (Na2SO4) and then evaporated. The residue was purified on silica gel column using a solvent system of hexanes/EtOAc: 3/1. Appropriate fractions were collected and evaporated to provide the title compound as colorless foam (0.21 g).

Workup

  1. customprepared
  2. customat room temperature
  3. waitat 80° C. for 0.5 h
  4. temperatureThe solution was cooled
  5. customThe layers were separated
  6. washThe organic layer was washed with brine (15 mL)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was purified on silica gel column
  10. customAppropriate fractions were collected
  11. customevaporated

Sources & evidence

ORD record
ord-27031f37390b41138f5b8a0c5b36d176
Source dataset
uspto-grants-2006_09
Patent number
US07105499B2

Reaction notes

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