Chlorotrimethylsilane → HCID 136773141, compound

HRID 2262391Notes

Reaction equation

HRID 2262391 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[O:12][C@@H:11]([N:23]2[C:33]3[N:32]=[C:30]([NH2:31])[NH:29][C:27](=[O:28])[C:26]=3[N:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si](Cl)(C)C.ClC([O:42][C:43]1C=CC=CC=1)=O.CO.[CH3:51][NH2:52]>N1C=CC=CC=1>[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:17])[CH3:18])[O:12][C@@H:11]([N:23]2[C:33]3[N:32]=[C:30]([NH:31][C:43](=[O:42])[NH:52][CH3:51])[NH:29][C:27](=[O:28])[C:26]=3[N:25]=[CH:24]2)[CH2:10]1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 15891Phenyl chloroformateHCID 57454252Monomethylamine methanolHCID 135542562HCID 135542562, compound

Product 1

HCID 136773141HCID 136773141, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

3′,5′-Bis-O-(tert-butyldimethylsilyl)deoxyguanosine (1.5 g, 3.02 mmol) was azeotroped with anhydrous pyridine three times and then dissolved in anhydrous pyridine (15 mL), and trimethylsilyl chloride (576 μL, 4.53 mmol) was added thereto. The mixture was stirred at room temperature for 1 hour, and then phenyl chloroformate (569 μL, 3.93 mmol) was added thereto. The mixture was stirred at room temperature for 4 hours. A 40% methylamine methanol solution (1.8 mL, 15.1 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hours. The reaction solution was extracted with ethyl acetate (200 mL)/water (150 mL) once and then with ethyl acetate (200 mL)/brine (150 mL) twice. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography with methanol/50% to 80% chloroform to give 3′,5′-bis-O-(tert-butyldimethylsilyl)-2-N-methylcarbamoyldeoxyguanosine (1.38 g, 78%).

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. extractionThe reaction solution was extracted with ethyl acetate (200 mL)/water (150 mL) once
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography with methanol/50% to 80% chloroform

Sources & evidence

ORD record
ord-e5947d789e6643b58f081e34abffc04a
Source dataset
uspto-grants-2010_12
Patent number
US07851157B1

Reaction notes

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