Reaction #87407

Reaction equation

water

Ethyl 2-(2-{[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]amino}-6-[(2,2,2-trifluoro-ethoxy)methyl]pyrimidin-4-yl)acetate

potassium cyanide

→

title compound

2-(2-{[3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]amino}-6-[(2,2,2-trifluoroethoxy)-methyl]pyrimidin-4-yl)acetamide

Solvents

ammonium hydroxide

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled down to rt
2. 2
   Extractionthe aqueous layer was extracted with DCM (5×)
3. 3
   DryingThe combined organic layers were dried over sodium sulfate
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was purified on a silica gel cartridge
6. 6
   Washeluting with 0% to 10% MeOH/DCM (1% ammonium hydroxide)

Procedure

Ethyl 2-(2-{[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]amino}-6-[(2,2,2-trifluoro-ethoxy)methyl]pyrimidin-4-yl)acetate (140 mg, 0.30 mmol, 1.0 eq) was suspended in ammonium hydroxide (3 mL) with few crystals of potassium cyanide in a sealed tube. The mixture was stirred 4 days at 65° C. The reaction mixture was cooled down to rt, water was added and the aqueous layer was extracted with DCM (5×). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified on a silica gel cartridge eluting with 0% to 10% MeOH/DCM (1% ammonium hydroxide) to give the title compound as a solid, 68 mg (50%).

Source