Ammonia → HCID 136773140, compound

HRID 2262395Notes

Reaction equation

HRID 2262395 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.[NH3:49]>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])[NH2:49])[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 222AmmoniaHCID 6397ChlorotrimethylsilaneHCID 15891Phenyl chloroformateHCID 135542562HCID 135542562, compound

Product 1

HCID 136773140HCID 136773140, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

3′,5′-Bis-O-(tert-butyldimethylsilyl)deoxyguanosine (2.8 g, 5.83 mmol) was azeotroped with anhydrous pyridine three times and then dissolved in anhydrous pyridine (60 mL), and trimethylsilyl chloride (1.11 mL, 8.75 mmol) was added thereto. The mixture was stirred at room temperature for 1 hour, and then phenyl chloroformate (1.10 mL, 8.75 mmol) was added thereto. The resulting mixture was stirred at room temperature for 4 hours, and 28% aqueous ammonia (4.1 mL, 29.1 mmol) was added thereto. The resulting mixture was stirred at room temperature for 2 hours. The reaction solution was extracted with ethyl acetate (250 mL)/water (200 mL) once and then with ethyl acetate (250 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 (25 g) with methanol/6% to 30% chloroform to give 3′,5′-bis-O-(tert-butyldimethylsilyl)-2-N-carbamoyldeoxyguanosine (2.12 g, 68%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 4 hours
  2. stirringThe resulting mixture was stirred at room temperature for 2 hours
  3. extractionThe reaction solution was extracted with ethyl acetate (250 mL)/water (200 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 (25 g) with methanol/6% to 30% chloroform

Sources & evidence

ORD record
ord-727559dfe8594fddbd0b53679ca14a1a
Source dataset
uspto-grants-2010_12
Patent number
US07851157B1

Reaction notes

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