Réaction #66633

Équation de réaction

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

CuCN

Water

→

5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzonitrile

Rendement 44.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Autrethe precipitate was collected
2. 2
   AutreThe residue was triturated with methanolic dichloromethane (10% CH3OH in CH2Cl2 with 0.1% NH4OH)
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe filtrate was concentrated
5. 5
   Autrepurified via flash chromatography (3% CH3OH in CH2Cl2 with 0.1% NH4OH)

Mode opératoire

A mixture of 5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (0.37 g, 0.925 mmol) and CuCN (0.12 g, 1.39 mmol) in DMF (5 ml) was heated at 120° C. for 3 hours. Water (100 ml) was added, and the precipitate was collected. The residue was triturated with methanolic dichloromethane (10% CH3OH in CH2Cl2 with 0.1% NH4OH) to release the product from its copper complex and filtered. The filtrate was concentrated and purified via flash chromatography (3% CH3OH in CH2Cl2 with 0.1% NH4OH) to give 5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzonitrile as white solid (0.12 g, 44%): M+H 300.

Source