Réaction #66679

Équation de réaction

4-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenol

(2-bromoethoxy)-tert-butyl-dimethyl silane

K2CO3

→

5-[5-Iodo-2-isopropyl-4-(2-trimethylsilanyloxy-ethoxy)-phenoxy]-pyrimidine-2,4-diamine

Rendement 97.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreSolvent was removed in vacuo
2. 2
   AutreThe residue was partitioned between methylene chloride and water
3. 3
   LavageThe combined organic extracts was washed with water
4. 4
   Séchagedried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Mode opératoire

A mixture of 4-(2,4-Diamino-pyrimidin-5-yloxy)-2-iodo-5-isopropyl-phenol (0.3 g, 0.78 mmol), (2-bromoethoxy)-tert-butyl-dimethyl silane (0.28 g, 1.17 mmol), and K2CO3 (0.22 g, 1.56 mmol) in anhydrous DMF (5 ml) was heated at 50° C. for 16 hrs. Solvent was removed in vacuo. The residue was partitioned between methylene chloride and water. The combined organic extracts was washed with water, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica (3% MeOH in methylene chloride with 0.1% NH4OH) gave 5-[5-Iodo-2-isopropyl-4-(2-trimethylsilanyloxy-ethoxy)-phenoxy]-pyrimidine-2,4-diamine (0.38 g, 90%) as a solid.

Source