Idoxuridine → HCID 67117228, compound

HRID 2364921Notes

Reaction equation

I[C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.C(N(CCCC)CCCC)CCC.[CH:31]([CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)=[CH2:32].C(Cl)(Cl)Cl>CN(C=O)C.O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO>[CH:33]1([CH:31]=[CH:32][C:2]2[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=2)[C@@H:7]2[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

Conditions

Temperature: 100 °C

Procedure

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).

Workup

customto obtain a suspension
customThereafter, the purification

Sources & evidence

ORD record: ord-14da68196f6e4770abe97cf824c80069
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697357B2

Reaction notes

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