Reaction #2452101

Reaction equation

CHCl3

Tributylamine

1-heptene

5-iodo-2′-deoxyuridine

→

5-heptene 2′-deoxyuridine

Yield 97.0%

Solvents

MeOH

dioxane

DMF

Conditions

Workup

1. 1
   Otherto obtain a suspension
2. 2
   Temperatureby heating by microwaves
3. 3
   Otherthe obtained sample was purified

Procedure

5-iodo-2′-deoxyuridine (1) (500 mg, 1.41 mmol) was dissolved in DMF (2.5 ml) and dioxane (2.5 ml), and palladium acetate (31 mg, 0.14 mmol) was added thereto to obtain a suspension. Tributylamine (340 μl, 1.41 mmol) and 1-heptene (5 ml, 3.53 mmol) were further added, and the reaction was carried out at 100° C. for 20 minutes by heating by microwaves. After confirming at least 90% decrease in the reaction materials by TLC (CHCl3:MeOH=9:1), the obtained sample was purified by using a silica gel column with a development solvent of CHCl3:MeOH=9:1. HU was found to be 445 mg, 1.36 mmol and the yield was 97%. The target compound was determined by 1H NMR for identification. In addition, mass analysis was carried out based on MALDI-TOF MS, and it was identified as the target compound (calcd. for C16H25N2O5 [M+H]+325.179, found 325.801).

Source