Reaction #66629

Reaction equation

4-chloro-5-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-pyrimidin-2-ylamine

aniline

Methylene chloride

→

5-(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-N4-phenyl-pyrimidine-2,4-diamine

Conditions

Workup

1. 1
   Otherwas placed in a sealed tube
2. 2
   Otherinsoluble solid was removed by filtration through celite
3. 3
   WashThe combined methylene chloride filtrate was washed with water
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   OtherAfter removal of the drying agent
6. 6
   Concentrationthe organic phase was concentrated under reduced pressure
7. 7
   OtherThe residue was purified with silica gel chromatography (2% methanol in methylene chloride)
8. 8
   Otherto yield a yellow oily residue, which
9. 9
   Otherwas further purified with preparative TLC and HPLC (5 to 100% acetonitrile in water with 0.1% trifluoroacetic acid

Procedure

A suspension of 4-chloro-5-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-pyrimidin-2-ylamine (0.043 g, 0.14 mmol) in aniline (4 ml) was placed in a sealed tube and heated at 100° C. over night. Methylene chloride was added and insoluble solid was removed by filtration through celite. The combined methylene chloride filtrate was washed with water and dried over anhydrous sodium sulfate. After removal of the drying agent, the organic phase was concentrated under reduced pressure. The residue was purified with silica gel chromatography (2% methanol in methylene chloride) to yield a yellow oily residue, which was further purified with preparative TLC and HPLC (5 to 100% acetonitrile in water with 0.1% trifluoroacetic acid to yield 5-(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-N4-phenyl-pyrimidine-2,4-diamine, M+H: 365.

Source