Dimethyl Sulfoxide → Acetic Acid 4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-formyl-tetrahydro-furan-3-yl Ester

HRID 642932

Reaction equation

HRID 642932 reaction equation
ClC(Cl)(Cl)C(OC(=O)C(Cl)(Cl)Cl)=O.CS(C)=O.[C:18]([Si:22]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[O:23][CH:24]1[CH:28]([CH2:29][OH:30])[O:27][CH:26]([N:31]2[CH:36]=[CH:35][C:34](=[O:37])[NH:33][C:32]2=[O:38])[CH:25]1[O:39][C:40](=[O:42])[CH3:41])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:18]([Si:22]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[O:23][CH:24]1[CH:28]([CH:29]=[O:30])[O:27][CH:26]([N:31]2[CH:36]=[CH:35][C:34](=[O:37])[NH:33][C:32]2=[O:38])[CH:25]1[O:39][C:40](=[O:42])[CH3:41])([CH3:19])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 20079Trichloroacetic anhydrideHCID 66774584Acetic Acid 4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-hydroxymethyl-tetrahydro-furan-3-yl Ester

Product 1

HCID 86594161Acetic Acid 4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-formyl-tetrahydro-furan-3-yl Ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of trichloroacetic anhydride (1.5 eq.) and dimethylsulfoxide (2.0 eq.) in dichloromethane at −78° C. is added a solution of Compound 9 in dichloromethane. After 30 minutes, triethylamine (4.5 eq.) is added. Subsequently, the mixture is poured into ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, and evaporated to dryness. The resulting material is carried into the next step without further purification. This procedure has been used to prepare the related 4′-C-α-formyl nucleosides (Nomura, M., et. al., J. Med. Chem. 1999, 42, 2901-2908).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe resulting material is carried into the next step without further purification
  5. customto prepare the related 4′-C-α-formyl nucleosides (Nomura, M., et. al., J. Med. Chem. 1999, 42, 2901-2908)

Sources & evidence

ORD record
ord-0df10ea6235445dca721d1d37702fc35
Source dataset
uspto-grants-2010_04
Patent number
US07696345B2

Linked notes

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