Phenol → HCID 91011440, compound

HRID 1889602Notes

Reaction equation

HRID 1889602 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([O-])([O-])=O.[Cs+].[Cs+].[C:48]1(O)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C1(C)C=CC=CC=1>[Si:30]([O:29][C@@H:28]1[C@@H:27]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[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][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:12]=3[N:13]=[CH:14]2)[CH2:17]1)([C:33]([CH3:35])([CH3:36])[CH3:34])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 24805984HCID 24805984, compound

Product 1

HCID 91011440HCID 91011440, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
105 °C

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) (63.2 mg, 0.106 mmol), Cs2CO3 (68.9 mg, 0.211 mmol) and phenol (19.9 mg, 0.211 mmol). Dry toluene (1.0 mL) was added and the reaction mixture was flushed with N2 and the mixture was allowed to stir at 105° C. for 2 h. The reaction mixture was filtered through Celite, the residue washed with Et2O and the filtrate evaporated to dryness. Chromatographic purification (SiO2, elution with 20% EtOAc in hexanes) afforded 50.5 mg (86% yield) of the title compound as a clear gum. Rf (20% EtOAc in hexanes)=0.21. 1H NMR (500 MHz, CDCl3): δ 8.49 (s, 1H, Ar—H), 8.40 (s, 1H, Ar—H), 7.45 (app t, 2H, Ar—H, Japp˜7.8), 7.29-7.26 (m, 3H, Ar—H), 6.53 (t, 1H, H-1′, J=6.3), 4.64 (m, 1H, H-3′), 4.04 (q, 1H, H-4′, J=3.4), 3.90 (dd, 1H, H-5′, J=11.2, 3.9), 3.70 (dd, 1H, H-5′, J=11.2, 2.7), 2.65 (app quint, 1H, H-2′, Japp˜6.3), 2.48 (ddd, 1H, H-2′, J=13.2, 6.1, 4.1), 0.92, 0.91 (2 s, 18H, tert-Bu), 0.10 (s, 12H, SiCH3). 13C NMR (126 MHz, CDCl3): δ 160.2, 152.5, 152.4, 152.0, 141.6, 129.6, 125.7, 122.1, 121.9, 88.0, 84.6, 71.8, 62.7, 41.5, 26.0, 25.7, 18.4, 18.0, −4.7, −4.8, −5.4, −5.5. FAB HRMS calcd for C28H45N4O4Si2 (M++H) 557.2979. found 557.2978.

Workup

  1. customIn a clean, dry
  2. customreaction
  3. customvial equipped with a stirring bar
  4. customthe reaction mixture was flushed with N2
  5. filtrationThe reaction mixture was filtered through Celite
  6. washthe residue washed with Et2O
  7. customthe filtrate evaporated to dryness
  8. customChromatographic purification (SiO2, elution with 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c5153d8980e447e7b1b7ea3fa8e558b5
Source dataset
uspto-grants-2013_08
Patent number
US08501931B2

Reaction notes

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