Methanol → 2'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridine

HRID 1157152Notes

Reaction equation

HRID 1157152 reaction equation
F.F.F.C(N(CC)CC)C.[Si]([O:28][CH2:29][C@H:30]1[O:34][C@@H:33]([N:35]2[CH:42]=[C:41]([CH3:43])[C:39](=[O:40])[NH:38][C:36]2=[O:37])[C@H:32]([O:44][CH2:45][CH2:46][O:47][N:48]([CH3:50])[CH3:49])[C@@H:31]1[OH:51])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CO>C1COCC1.C(Cl)Cl>[CH3:49][N:48]([CH3:50])[O:47][CH2:46][CH2:45][O:44][C@@H:32]1[C@H:31]([OH:51])[C@@H:30]([CH2:29][OH:28])[O:34][C@H:33]1[N:35]1[CH:42]=[C:41]([CH3:43])[C:39](=[O:40])[NH:38][C:36]1=[O:37]

Participants

6

Reactant 3

HCID 887MethanolHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 229477015'-O-tert-butyldiphenylsilyl-2'-O-[N,N-dimethylaminooxyethyl)-5-methyluridine

Product 1

HCID 229476992'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridineYield 92.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and TEA (1.67 mL, 12 mmol, dry, stored over KOH) and added to 5′-O-tert-butyldiphenylsilyl-2′-O—[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol). The reaction was stirred at room temperature for 24 hrs and monitored by TLC (5% MeOH in CH2Cl2). The solvent was removed under vacuum and the residue purified by flash column chromatography (eluted with 10% MeOH in CH2Cl2) to afford 2′-O-(dimethylaminooxyethyl)-5-methyluridine (766 mg, 92.5%) upon rotary evaporation of the solvent.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue purified by flash column chromatography (eluted with 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a8fb27b2f1034137a1f22871bbd6869f
Source dataset
uspto-grants-2010_10
Patent number
US07807649B2

Reaction notes

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