Dimethylformamide dimethyl acetal → 5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-(N,N-dimethylaminomethylene)-2'-oxo-uridine

HRID 234976Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C:12](=[O:23])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO[CH:26](OC)[N:27]([CH3:29])[CH3:28]>CN(C)C=O>[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C:12](=[O:23])[C:11]1=[CH:26][N:27]([CH3:29])[CH3:28])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-2'-oxo-uridine (2.2 g, 6.45 mmol) was dissolved in 25 mL of dry dimethylformamide (DMF) and 0.85 g (7.1 mmol) of N,N-dimethylformamide dimethyl acetal was added. The reaction mixture was heated to 50° C. under a nitrogen atmosphere and stirred for 0.5 h. The solvent was removed in vacuo and the residue (3.2 g) was dissolved in methylene chloride and purified by flash chromatography (5 psi) on a silica gel column (2×25 cm) eluted with 200 mL of methylene chloride, 200 mL of 2% methanol in methylene chloride and 200 mL of 5% methanol in methylene chloride to give 1.78 g (70% yield) of the title compound MS DCI: 396 (M+H)+, 418 (M+Na)+

Workup

customThe solvent was removed in vacuo
dissolutionthe residue (3.2 g) was dissolved in methylene chloride
custompurified by flash chromatography (5 psi) on a silica gel column (2×25 cm)
washeluted with 200 mL of methylene chloride, 200 mL of 2% methanol in methylene chloride and 200 mL of 5% methanol in methylene chloride

Sources & evidence

ORD record: ord-cbd6a5f1937042d793336d2de49f7ef8
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05597824

Reaction notes

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