Trimethylsilyl triflate → 4-Chloro-1-(2-O-methyl-3,5-di-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

HRID 2210631Notes

Reaction equation

HRID 2210631 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]CC[Si](C)(C)C)[N:3]=1.[CH3:15][O:16][C@@H:17]1[C@H:30]([O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:29]([CH2:40][O:41][C:42](=[O:49])[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:28][C@@H:18]1OC(=O)C1C=CC=CC=1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C@@H:18]2[O:28][C@H:29]([CH2:40][O:41][C:42](=[O:49])[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@@H:30]([O:31][C:32](=[O:39])[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C@H:17]2[O:16][CH3:15])[C:4](=[O:8])[N:3]=1

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 102632784-Chloro-2-(2-trimethylsilanyl-ethoxy)-pyrimidineHCID 10917755(-)-Inosine Dehydroxy-N-(6-iminohexyl)-2,2,2-trifluoroacetamide

Product 1

HCID 217824984-Chloro-1-(2-O-methyl-3,5-di-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Chloro-2-trimethylsilylethoxy-pyrimidine (3.5 g, 15.2 mmole) and 2-O-methyl-1,3,5-tri-O-benzoyl-α-D-ribose (7.0 g, 15.2 mmole) were dissolved in acetonitrile (100 ml). This solution was treated with trimethylsilyl trifluoromethanesulfonate (2.8 g, 15.2 mmole) and stirred for 1.5 hours. The reaction mixture was concentrated to an oil and redissolved in 300 ml CH2Cl2. The CH2Cl2 solution was washed with cold concentrated sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated to an oil. The oil was coevaporated with acetonitrile and dried to a brown foam to give 6.70 g (91%) crude product.

Workup

  1. concentrationThe reaction mixture was concentrated to an oil
  2. dissolutionredissolved in 300 ml CH2Cl2
  3. washThe CH2Cl2 solution was washed with cold concentrated sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil
  7. customdried to a brown foam

Sources & evidence

ORD record
ord-28f666b72fb4495ba2c9b198afa6f7c7
Source dataset
uspto-grants-1995_10
Patent number
US05459243

Reaction notes

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