Reaktion #168967

Reaktionsgleichung

NaOH

5-(5-amino-2-Isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

2,5-dimethoxypyran

→

5-(2-isopropyl-4-methoxy-5-pyrrol-1-yl-phenoxy)-pyrimidine-2,4-diamine

Ausbeute 72.0%

Lösungsmittel

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was warmed to reflux
2. 2
   TemperaturAfter 2 h the solution was cooled
3. 3
   Extraktionextracted with ethyl acetate (3×75 mL)
4. 4
   WaschenThe combined organics were washed with H2O
5. 5
   Waschenwashed with brine
6. 6
   Trocknendried with Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigeto give a brown solid
10. 10
    SonstigePurification via flash chromatography (CH2Cl2/MeOH 97:3)

Vorschrift

To a solution of 5-(5-amino-2-Isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (0.303 g, 1.0 mmol) in 15 mL AcOH was added 2,5-dimethoxypyran (0.152 g, 1.2 mmol). The solution was warmed to reflux. After 2 h the solution was cooled and poured over ice/H2O. The solution was converted to pH=8 with 50% NaOH and extracted with ethyl acetate (3×75 mL). The combined organics were washed with H2O, washed with brine, dried with Na2SO4, filtered and concentrated in vacuo to give a brown solid. Purification via flash chromatography (CH2Cl2/MeOH 97:3) afforded 5-(2-isopropyl-4-methoxy-5-pyrrol-1-yl-phenoxy)-pyrimidine-2,4-diamine (0.244 g, 72%) as a pale yellow solid. (M+H)=340.

Quelle