Cesium carbonate → HCID 91567551, compound

HRID 1889598Notes

Reaction equation

HRID 1889598 reaction equation
N1([O:10][C:11]2[C:12]3[N:13]=[CH:14][N:15]([C:38]=3[N:39]=[CH:40][N:41]=2)[C@@H:16]2[O:37][C@H:27]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C@@H:18]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:17]2)C2C=CC=CC=2N=N1.[C:42]([O-])([O-])=O.[Cs+].[Cs+]>CO>[Si:30]([O:29][C@@H:28]1[C@@H:27]([CH2:18][O:19][Si:20]([C:23]([CH3:25])([CH3:26])[CH3:24])([CH3:22])[CH3:21])[O:37][C@@H:16]([N:15]2[C:38]3[N:39]=[CH:40][N:41]=[C:11]([O:10][CH3:42])[C:12]=3[N:13]=[CH:14]2)[CH2:17]1)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 24805984HCID 24805984, compound

Product 1

HCID 91567551HCID 91567551, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a clean, dry reaction vial equipped with a stirring bar were placed O6-(benzotriazol-1-yl)-3′,5′-bis-O-(tert-butyldimethylsilyl)-2′-deoxyinosine (26) (59.8 mg, 0.100 mmol), Cs2CO3 (65.2 mg, 0.200 mmol) and methanol (1.0 mL). The reaction mixture was flushed with N2 and stirred at room temperature for 1 h after which the mixture was evaporated to dryness. Chromatographic purification (SiO2, elution with 20% EtOAc in hexanes) afforded 38 mg (77% yield) of the title compound as a clear gum. Rf (20% EtOAc in hexanes)=0.12. 1H NMR (500 MHz, CDCl3): δ 8.52 (s, 1H, Ar—H), 8.27 (s, 1H, Ar—H), 6.49 (t, 1H, H-1′, J=6.3), 4.62 (m, 1H, H-3′), 4.18 (s, 3H, OCH3), 4.01 (q, 1H, H-4′, J=3.4), 3.87 (dd, 1H, H-5′, J=11.2, 3.9), 3.77 (dd, 1H, H-5′, J=11.2, 2.9), 2.62 (app quint, 1H, H-2′, Japp˜6.3), 2.45 (ddd, 1H, H-2′, J=13.2, 6.4, 3.9), 0.91 (s, 18H, tert-Bu), 0.09, 0.08 (2 s, 12H, SiCH3). 13C NMR (126 MHz, CDCl3): δ 161.1, 152.0, 151.5, 140.6, 122.0, 88.0, 84.5, 71.9, 62.8, 54.0, 41.4, 25.9, 25.7, 18.4, 17.9, −4.7, −4.8, −5.5, −5.6. FAB HRMS calcd for C23H43N4O4Si2 (M++H) 495.2823. found 495.2798.

Workup

  1. customIn a clean, dry
  2. customreaction
  3. customvial equipped with a stirring bar
  4. customThe reaction mixture was flushed with N2
  5. customwas evaporated to dryness
  6. customChromatographic purification (SiO2, elution with 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b36a8d255c154ee6a0bf9b925aaa5bb0
Source dataset
uspto-grants-2013_08
Patent number
US08501931B2

Reaction notes

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