HCID 18394974, compound → 5-(9-ethylcarbazol-3-ylmethyl)-2',3',5'-tris-O-((1,1-dimethylethyl)dimethylsilyl)uridine

HRID 1602961Notes

Reaction equation

HRID 1602961 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH:16](O)[C:17]3[C:18](=[O:54])[NH:19][C:20](=[O:53])[N:21]([CH:52]=3)[C@@H:22]3[O:51][C@H:41]([CH2:42][O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[C@@H:32]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[C@H:23]3[O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]>C(O)C.[Pd]>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH2:16][C:17]3[C:18](=[O:54])[NH:19][C:20](=[O:53])[N:21]([CH:52]=3)[C@@H:22]3[O:51][C@H:41]([CH2:42][O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[C@@H:32]([O:33][Si:34]([C:37]([CH3:38])([CH3:39])[CH3:40])([CH3:35])[CH3:36])[C@H:23]3[O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

4

Reactant 1

HCID 18394974HCID 18394974, compound

Product 1

HCID 183949765-(9-ethylcarbazol-3-ylmethyl)-2',3',5'-tris-O-((1,1-dimethylethyl)dimethylsilyl)uridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product of step (i) (15.83 g) was subjected to hydrogenolysis at 2.5 atmospheres in ethanol (200 ml) using 10% palladium on charcoal (1 g) until reaction was complete by thin layer chromatographical analysis. The catalyst was filtered and the mother liquor collected. The solvent was removed under reduced pressure. The remaining residue was purified by flash silica-gel chromatography to afford 5-(9-ethylcarbazol-3-ylmethyl)-2',3',5'-tris-O-((1,1-dimethylethyl)dimethylsilyl)uridine as a yellow foam.

Workup

  1. customuntil reaction
  2. filtrationThe catalyst was filtered
  3. customthe mother liquor collected
  4. customThe solvent was removed under reduced pressure
  5. customThe remaining residue was purified by flash silica-gel chromatography

Sources & evidence

ORD record
ord-e15a29b02d5f4743bd079e2c1c8f4afd
Source dataset
uspto-grants-1999_11
Patent number
US05985849

Reaction notes

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