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

HRID 1871855Notes

Reaction equation

HRID 1871855 reaction equation
F.F.F.C(N(CC)CC)C.C(N(CC)CC)C.[Si]([CH:35]([OH:58])[C@H:36]1[O:40][C@@H:39]([N:41]2[CH:48]=[C:47]([CH3:49])[C:45](=[O:46])[NH:44][C:42]2=[O:43])[C@H:38]([O:50][CH2:51][CH2:52][O:53][N:54]([CH3:56])[CH3:55])[C@@H:37]1[OH:57])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CO>C1COCC1.C(Cl)Cl>[CH3:55][N:54]([CH3:56])[O:53][CH2:52][CH2:51][O:50][C@@H:38]1[C@H:37]([OH:57])[C@@H:36]([CH2:35][OH:58])[O:40][C@H:39]1[N:41]1[CH:48]=[C:47]([CH3:49])[C:45](=[O:46])[NH:44][C:42]1=[O:43]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 21970134HCID 21970134, compound

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 triethylamine (1.67 mL, 12 mmol, dry, kept over KOH). This mixture of triethylamine-2HF was then added to 5'-tert-butyldiphenylsilyl-2'-O-[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and stirred at room temperature for 24 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Solvent was removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get 2'-O-(dimethylaminooxyethyl)-5-methyluridine (766 mg, 92.5%).

Workup

  1. customReaction
  2. customSolvent was removed under vacuum
  3. washeluted with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-937c296b6dde457d911b7ff81d77d4cc
Source dataset
uspto-grants-2000_08
Patent number
US06107091

Reaction notes

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