Hydrazine hydrate (1:1) → 5-Fluoro-4-hydrazino-2-methyl-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]pyrimidine

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Reaction Steps

To a mixture of 4,6-dichloro-5-fluoro-2-methylpyrimidine (90 mg, 0.50 mmol), 1-(3-methyl-3-azetidinyl)pyrrolidine dihydrochloride (Example 176) (131 mg, assumed 86% pure, 0.53 mmol) in 5 mL of DMSO was added DIPEA (0.345 mL, 1.98 mmol). The resulting reaction mixture was stirred at rt overnight, and then hydrazine monohydrate was added (0.5 mL) and the contents were heated to 80° C. for 4 h. The reaction mixture was then cooled to room temperature and purified by RP-HPLC to provide 5-fluoro-4-hydrazino-2-methyl-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]pyrimidine (100 mg, 71%). LCMS: (M+H)+: 281.0.

Provenance & Evidence