Reaction #87447

Reaction equation

sodium triacetoxyborohydride

Dimethylamine

acetic acid

2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine-4-carbaldehyde

→

title compound

4-((Dimethylamino)methyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-2-amine

Solvents

Water

DCE

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred for 3 minutes
2. 2
   Otherthe phases were separated
3. 3
   ExtractionThe water phase was extracted by DCM
4. 4
   DryingThe combined organic layer was dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated on silica
7. 7
   Washeluting with a gradient of methanol in DCM
8. 8
   OtherThe solvents were evaporated
9. 9
   Otherthe residue was purified by preparative HPLC

Procedure

2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine-4-carbaldehyde (100 mg, 0.24 mmol) was dissolved in DCE (4 mL). Dimethylamine (2 M in THF, 0.142 mL, 0.28 mmol) and acetic acid (0.014 mL, 0.24 mmol) were added followed by sodium triacetoxyborohydride (80 mg, 0.38 mmol). The mixture was stirred at rt under nitrogen atmosphere for 1 hour 45 min. Water was added and the mixture was stirred for 3 minutes then the phases were separated. The water phase was extracted by DCM. The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on silica then subjected to column chromatography eluting with a gradient of methanol in DCM. The solvents were evaporated and the residue was purified by preparative HPLC to give the title compound as a dry film, 22 mg (21%).

Source