Trimethylsilyl triflate → HCID 10746734, compound

HRID 2271259Notes

Reaction equation

HRID 2271259 reaction equation
[CH2:1]([Si:3]([C:8]#[C:9][C@:10]1([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:18][CH:13](OC(=O)C)[C@H:12]([O:19][C:20](=[O:22])[CH3:21])[C@@H:11]1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].N[C:41]1[NH:49][C:48]2[C:43](=[N:44][C:45]([NH2:50])=[N:46][CH:47]=2)[N:42]=1.C/C(/O[Si](C)(C)C)=[N:53]\[Si](C)(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(=O)([O-])O.[Na+]>ClCCCl>[C:20]([O:19][C@@H:12]1[C@H:11]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@:10]([C:9]#[C:8][Si:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[CH2:1][CH3:2])([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:18][C@H:13]1[N:42]1[CH:41]=[N:49][C:48]2[C:43]1=[N:44][C:45]([NH2:50])=[N:46][C:47]=2[NH2:53])(=[O:22])[CH3:21]

Participants

7

Reactant 5

HCID 65367Trimethylsilyl triflateHCID 2439487h-purine-2,8-diamineHCID 516892Sodium BicarbonateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 12042250HCID 12042250, compound

Product 1

HCID 10746734HCID 10746734, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of Compound 6 (1.1 g, 2 mmol) in 1,2-dichloroethane (16.5 ml), diaminopurine (0.45 g, 3 mmol) and N,O-bis(trimethylsilyl)acetamide (4.4 ml, 18 mmol) were added, followed by refluxing for three hours. After the mixture was cooled to room temperature, trimethylsilyl trifluoromethanesulfonate (0.77 ml, 4 mmol) was added dropwise to the mixture at 0° C. in an argon atmosphere. The mixture was stirred for 15 minutes at room temperature, refluxed for 24 hours, and cooled to room temperature. A saturated aqueous solution of sodium hydrogencarbonate was added thereto at 0° C., followed by stirring for 15 minutes at room temperature. Insoluble materials were separated through filtration by use of Celite, and then the organic layer was separated from the filtrate. After an aqueous layer was extracted with chloroform once, the organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was applied to a silica gel column (20 g, eluent; ethyl acetate:n-hexane:ethanol=20:10:1), to thereby yield Compound 25 in an amount of 0.85 g (66%).

Workup

  1. temperatureby refluxing for three hours
  2. temperaturerefluxed for 24 hours
  3. temperaturecooled to room temperature
  4. customat 0° C.
  5. stirringby stirring for 15 minutes at room temperature
  6. customInsoluble materials were separated through filtration by use of Celite
  7. customthe organic layer was separated from the filtrate
  8. extractionAfter an aqueous layer was extracted with chloroform once
  9. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d7d78317c7c94b3194f0821bf4853111
Source dataset
uspto-grants-2001_12
Patent number
US06333315B1

Reaction notes

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