Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Idoxuridine | HCID 5905 | — |
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Tributylamine | HCID 7622 | — |
| Reactant | Vinylcyclohexane | HCID 12757 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67117228 | HCID 67117228 | 84% |
Reaction Steps
5-iodo-2′-deoxyuridine (1) (505 mg, 1.42 mmol) was dissolved in DMF (2.5 ml) and dioxane (2.5 ml), and palladium acetate (33 mg, 0.14 mmol) was added thereto to obtain a suspension. Tributylamine (340 μl, 1.41 mmol) and vinylcyclohexane (2.0 ml, 14.1 mmol) were further added to the mixture, which was heated by microwaves for the reaction at 100° C. for 20 minutes. Disappearance of the raw materials was confirmed by TLC (CHCl3:MeOH=9:1). Thereafter, the purification was carried out by using a silica gel column with the development solvent of CHCl3 and MeOH(CHCl3:MeOH=9:1). (2b) was found to be 400 mg, 1.19 mmol and the yield was 84%. The target compound was determined by 1H NMR for identification. Further, mass analysis was carried out by MALDI-TOF MS and it was identified as the target compound (calcd. for C17H25N2O5 [M+H]+ 337.176, found 337.156).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08697357B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-14da68196f6e4770abe97cf824c80069 |
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| Source note | uspto-grants-2014_04 |
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