Tetrabutylammonium Fluoride → 8-(3-Pyridinyl)adenosine

HRID 1689622Notes

Reaction equation

HRID 1689622 reaction equation
[Si]([O:8][C@@H:9]1[C@H:13]([O:14][Si](C(C)(C)C)(C)C)[C@@H:12]([CH2:22][O:23][Si](C(C)(C)C)(C)C)[O:11][C@H:10]1[N:31]1[C:40]2[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=2[N:33]=[C:32]1[C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[N:43]1[CH:44]=[CH:45][CH:46]=[C:41]([C:32]2[N:31]([C:40]3[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=3[N:33]=2)[C@@H:10]2[O:11][C@H:12]([CH2:22][OH:23])[C@@H:13]([OH:14])[C@H:9]2[OH:8])[CH:42]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 669067752',3',5'-Tris-o-(tert-butyldimethylsilyl)-8-(3-pyridinyl)adenosine

Product 1

HCID 669064258-(3-Pyridinyl)adenosine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2′,3′,5′-tris-O-(tert-butyldimethylsilyl)-8-(3-pyridinyl)adenosine (16c) (0.56 g, 0.82 mmol) and TBAF (0.85 g, 3.26 mmol) in THF (31 ml) under argon was stirred at room temperature overnight. The solvent was distilled off and the residual material dissolved in MeOH (10 ml). The solution was left at 0° C. overnight and the title compound isolated by filtration. 13C NMR: (75 MHz, DMSO); δ 62.27 (C-5′), 71.13/71.62 (C-2′, C-3′), 86.95/89.27 (C-4, C-1), 119.33/123.69/125.71/137.20/148.20/149.80/149.85/150.88/152.33/156.34 (C-5, C-5″, C-3″, C-4″, C-6, C-8, C-6″, C-2″, C-2, C-4). MS (EI): 344 (M, 2%), 255 (5), 241 (5), 213 (22), 212 (100), 211 (5) 185 (12), 104 (12).

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe residual material dissolved in MeOH (10 ml)

Sources & evidence

ORD record
ord-2feb1e3ce04442feaeb3e05f54cb03dc
Source dataset
uspto-grants-2012_04
Patent number
US08153609B2

Reaction notes

Loading…