Réaction #66632

Équation de réaction

iodine monochloride

5-(2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

iodine monochloride

NaHCO3

Water

→

5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

Rendement 93.0%

Solvants

acetic acid

acetic acid

acetic acid

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe reaction mixture was stirred for an additional hour at room temperature
2. 2
   Extractionextracted into dichloromethane
3. 3
   SéchageThe organic layer was dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe residue was purified via flash chromatography (5% CH3OH in CH2CL2 with 0.1% NH4OH)

Mode opératoire

To a solution of 5-(2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (0.40 g, 1.44 mmol) in glacial acetic acid (4 ml) at room temperature was added a solution of iodine monochloride (0.28 g, 1.76 mmol) in glacial acetic acid (4 ml). Water (6 ml) was also added, and the reaction was stirred for 16 hours, after which another portion of iodine monochloride (0.4 g, 2.47 mmol) in glacial acetic acid (4 ml) was added. The reaction mixture was stirred for an additional hour at room temperature. The acidic mixture was basified with saturated NaHCO3 solution and extracted into dichloromethane. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash chromatography (5% CH3OH in CH2CL2 with 0.1% NH4OH) to give 5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine as beige colored solid (0.536 g, 92%). M+H 400.

Source