Adenine → HCID 10604013, compound

HRID 2271257Notes

Reaction equation

HRID 2271257 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:40]1[C:48]([NH2:49])=[C:47]2[C:43]([N:44]=[CH:45][NH:46]2)=[N:42][CH:41]=1.C/C(/O[Si](C)(C)C)=N\[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:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@:10]([C:9]#[C:8][Si:3]([CH2:6][CH3:7])([CH2:4][CH3:5])[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:44]1[C:43]2[N:42]=[CH:41][N:40]=[C:48]([NH2:49])[C:47]=2[N:46]=[CH:45]1)(=[O:22])[CH3:21]

Participants

7

Reactant 5

HCID 190AdenineHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 12042250HCID 12042250, compound

Product 1

HCID 10604013HCID 10604013, 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), adenine (0.405 g, 3 mmol) and N,O-bis(trimethylsilyl)acetamide (2.7 ml, 11 mmol) were added, followed by refluxing for 1.5 hours. After the mixture was allowed to cool to room temperature, trimethylsilyl trifluoromethanesulfonate (0.77 ml, 4 mmol) was added dropwise to the mixture under stirring at 0° C. in an argon atmosphere. The mixture was stirred for 15 minutes at room temperature, refluxed for 24 hours, and allowed to cool 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 removed through filtration by use of Celite, and then the organic layer was separated from the filtrate. After an aqueous layer was extracted with chloroform, the organic layer was washed once with a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and concentrated through distillation under reduced pressure, so as to evaporate the solvent. The residue was applied to a silica gel column (15 g, eluent; ethyl acetate:n-hexane:ethanol=20:20:1), to thereby yield Compound 20 in an amount of 0.69 g (55%).

Workup

  1. temperatureby refluxing for 1.5 hours
  2. stirringThe mixture was stirred for 15 minutes at room temperature
  3. temperaturerefluxed for 24 hours
  4. temperatureto cool to room temperature
  5. customat 0° C.
  6. stirringby stirring for 15 minutes at room temperature
  7. customInsoluble materials were removed through filtration by use of Celite
  8. customthe organic layer was separated from the filtrate
  9. extractionAfter an aqueous layer was extracted with chloroform
  10. washthe organic layer was washed once with a saturated aqueous solution of sodium hydrogencarbonate
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated through distillation under reduced pressure
  13. customso as to evaporate the solvent

Sources & evidence

ORD record
ord-96d882c279f040bba761eec7279181bb
Source dataset
uspto-grants-2001_12
Patent number
US06333315B1

Reaction notes

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