Imidazole → 5′-O-[(1,1-Dimethylethyl)dimethylsilyl]-5-methyluridine

HRID 2209764Notes

Reaction equation

HRID 2209764 reaction equation
[CH3:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9].N1C=CN=C1.[C:24]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])([CH3:26])[CH3:25]>>[Si:28]([O:14][CH2:13][C@H:12]1[O:15][C@@H:7]([N:6]2[CH:16]=[C:2]([CH3:1])[C:3](=[O:18])[NH:4][C:5]2=[O:17])[C@H:8]([OH:9])[C@@H:10]1[OH:11])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:30])[CH3:29]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 4454085-Methyluridine

Product 1

HCID 143317235′-O-[(1,1-Dimethylethyl)dimethylsilyl]-5-methyluridineYield 73%

Procedure

A solution of 5-methyluridine (1.42 g, 5.49 mmol), imidazole (0,816 g, 11.26 mmol) and tertbutyldimethylsilyl chloride (0.9 g, 6.01 mmol) was stirred at room temperature for 24 hours and then concentrated in vacuo. The residue obtained was purified by chromatography on a silica gel column using CHCl3 -methanol (30:1) as the eluent to give 1.49 g (73%) of 5'-O-tert-butyldimethylsilyl-5-methyluridine as a colorless solid: mp 209°-211° C. (ethyl acetate); 1H NMR (DMSO-d6) δ 0.0 (6H, s, (CH3)2Si), 0.81 (9H, s, (CH3)3CSi), 3.60-3.90 (5H, m, 2, 3, 4' and 5'-H), 4.97 (1H, d, J=4.39 Hz, 3'-OH, exchangeable), 5.25 (1H, d, J=5.57 Hz, 2'-OH, exchangeable), 5.71 (1H, d, J=5.57 Hz, 1'-H), 7.32 (1H, s, 6-H), 11.21 (1H, s, NH, exchangeable).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-b73be53ee7b34507baaf757be93e2e1c
Source dataset
uspto-grants-1995_10
Patent number
US05455339

Reaction notes

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