Triethylamine → HCID 512010, compound

Temperature

70 °C

A solution of triethylamine (3.9 mL, 28.2 mmol) in dioxane (12 mL) was deareated by bubbling nitrogen through for 15 min. Palladium acetate (0.60 g, 0.26 mmol) and triphenylphosphine (0.183 g, 0.70 mmol) were added and the solution was heated at 70° C. for 20 min to give a dark brown solution. 5-Iodo-3′-deoxyuridine (5.0 g, 14.1 mmol) and methyl 2,4-pentadienoate (2.5 g, 22.3 mmol) was added and the mixture was heated under reflux for 15 h. The solvent and volatile components were evaporated in vacuo and the residue was partitioned between water (15 mL) and EtOAc (15 mL). The phases were separated and the aqueous phase was extracted twice with EtOAc (10 mL each). The combined organic phase was washed with brine and concentrated. The residue was dissolved in MeOH (15 mL) and allowed to cool to room temperature. The solid formed was collected by filtration, washed with a small quantity of MeOH and dried in vacuo to give 0.38 g brown powder.

1. customby bubbling nitrogen through for 15 min
2. customto give a dark brown solution
3. temperaturethe mixture was heated
4. temperatureunder reflux for 15 h
5. customThe solvent and volatile components were evaporated in vacuo
6. customthe residue was partitioned between water (15 mL) and EtOAc (15 mL)
7. customThe phases were separated
8. extractionthe aqueous phase was extracted twice with EtOAc (10 mL each)
9. washThe combined organic phase was washed with brine
10. concentrationconcentrated
11. dissolutionThe residue was dissolved in MeOH (15 mL)
12. temperatureto cool to room temperature
13. customThe solid formed
14. filtrationwas collected by filtration
15. washwashed with a small quantity of MeOH
16. customdried in vacuo

ORD record

ord-fb0a025b96b1416c8a597865cbdc7f4e

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07605144B2