Dimethylformamide dimethyl acetal → HCID 10434757, compound

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Reaction Steps

[4-(4-Ethyl-piperazin-1-ylmethyl)-phenyl]-[4-(3-p-tolyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amine (Example 101) (165 mg; 0.364 mMol) is suspendend in toluene (3 mL) and treated with DMF-DMA (168 mg; 1.32 mMol, 187 μL) at rt. The mixture is stirred at reflux for a total of 102 h whereby additional DMF-DMA is added after 48 h (187 μL), after 61 h (187 μL) and after 82 h (374 μL). Upon completion of the reaction and cooling to rt the solvent is removed under reduced pressure. The crude product mixture is purified by reversed phase chromatography (Lichroprep® RP18 15-25 μM; eluting with 18% CH3CN (0.1% TFA)/82% H2O (0.1% TFA)). The pure fractions 27-34 are combined and evaporated. The residue is dissolved in H2O (2 mL) and neutralized with 1N NaOH. The crystalline product (free base) is filtered off, washed with H2O and dried at 60° C. to obtain the title compound as beige crystalline powder.

Provenance & Evidence