Dimethylformamide → HCID 136773142, compound

HRID 2262399Notes

Reaction equation

HRID 2262399 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].[H-].[Na+].C[S:37]N=C=O.C([O-])(=O)C.[NH4+].[CH3:46][N:47]([CH3:50])C=O>C1(C)C=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:46](=[S:37])[NH:47][CH3:50])[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

7

Reactant 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 517165Ammonium AcetateHCID 21933440MethylthioisocyanateHCID 135542562HCID 135542562, compound

Product 1

HCID 136773142HCID 136773142, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

3′,5′-Bis-O-(tert-butyldimethylsilyl)deoxyguanosine (3.0 g, 6.05 mmol) was azeotroped with anhydrous toluene three times and then dissolved in anhydrous dimethylformamide (30 mL), and then sodium hydride (199 mg, 7.86 mmol) was added thereto. The mixture was stirred at 70° C. for 1 hour. Then, the reaction solution was returned to room temperature, and methyl thioisocyanate (1.24 mL, 18.2 mmol) was added thereto. The mixture was stirred at 70° C. for 36 hours. The reaction solution was poured into a 0.5 M ammonium acetate buffer solution (150 mL), and the resulting mixture was extracted with ethyl acetate (200 mL)/0.5 M ammonium acetate buffer solution (150 mL) once and then with ethyl acetate (200 mL)/water (150 mL) twice. The organic layer was evaporated under reduced pressure, and the residue was subjected to NH silica gel column chromatography to remove raw materials with methanol/5% chloroform. The gel was collected and eluted with methanol/80% chloroform 40 times. The eluate was concentrated to give 3′,5′-bis-O-(tert-butyldimethylsilyl)-2-N-methylthiocarbamoyldeoxyguanosine (1.65 g, 48%).

Workup

  1. customwas returned to room temperature
  2. stirringThe mixture was stirred at 70° C. for 36 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate (200 mL)/0.5 M ammonium acetate buffer solution (150 mL) once
  4. customThe organic layer was evaporated under reduced pressure
  5. customto remove raw materials with methanol/5% chloroform
  6. customThe gel was collected
  7. washeluted with methanol/80% chloroform 40 times
  8. concentrationThe eluate was concentrated

Sources & evidence

ORD record
ord-02067e1e597042968572d2dd8d102bb4
Source dataset
uspto-grants-2010_12
Patent number
US07851157B1

Reaction notes

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