Dimethyl Sulfoxide → Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(4-methyl-1-piperazinyl)(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate

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Reaction Steps

4-Methyl-N-(1,3-thiazol-2-ylmethyl)-1-piperazinamine (2.2169 g, 10.44 mmol) was dissolved in THF (30 mL) and triethylamine (4.37 ml, 31.3 mmol). Then tris(1,1-dimethylethyl)2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate (3.89 g, 7.83 mmol) and DMSO (5 mL) were added. The reaction was left to stir overnight. The THF was evaporated away, and the mixture was diluted with water. The aqueous layer was extracted with ethyl acetate, and the organics were dried (Na2SO4) and evaporated. Purification by silica gel chromatography and RP-HPLC provided tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(4-methyl-1-piperazinyl)(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate (0.2014 g, 3%). LCMS: (M+H)+=674.6.

Provenance & Evidence