Reaktion #87447

Reaktionsgleichung

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

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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

Lösungsmittel

Water

DCE

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

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