Idoxuridine → HCID 6479134, compound
Reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C.I[C:28]1[C:29](=[O:43])[NH:30][C:31](=[O:42])[N:32]([CH:41]=1)[C@@H:33]1[O:40][C@H:37]([CH2:38][OH:39])[C@@H:35]([OH:36])[CH2:34]1.[CH3:44][O:45][C:46](=[O:49])[CH:47]=[CH2:48]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:46](/[CH:47]=[CH:48]/[C:28]1[C:29](=[O:43])[NH:30][C:31](=[O:42])[N:32]([CH:41]=1)[C@@H:33]1[O:40][C@H:37]([CH2:38][OH:39])[C@@H:35]([OH:36])[CH2:34]1)([O:45][CH3:44])=[O:49]Participants
7
Conditions
- Temperature
- 70 °C
Procedure
A mixture of Pd(OAc)2 (0.316 g, 1.41 mmol), PPh3 (0.741 g, 2.82 mmol), and triethylamine (4.9 mL) in 1,4-dioxane (50 mL) was stirred at 70° C. until an intense red colour had developed. To this 5-iodo-2′-deoxyuridine (10 g, 28.24 mmol) and methylacrilate (4.862 g, 56.48 mmol, 5.1 mL) in 1,4-dioxane (20 mL) were added and the mixture stiffed at refluxed for 30 mins. The reaction was filtered while still hot and the 20 filtrate cooled over night at 4° C. The resulting pale yellow precipitate was filtered, washed with DCM and dried in vacuo to give the product as white solid (6.2 g, yield 70.7%).
Workup
- temperatureat refluxed for 30 mins
- filtrationThe reaction was filtered while still hot and the 20 filtrate
- temperaturecooled over night at 4° C
- filtrationThe resulting pale yellow precipitate was filtered
- washwashed with DCM
- customdried in vacuo
Sources & evidence
- ORD record
- ord-218776c5177b407092d5f537fcde3183
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951787B2
Reaction notes
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