Cl[C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[C:4]([CH3:10])[N:3]=1.[NH:11]1[CH2:15][CH:14]=[CH:13][CH2:12]1.CCN(C(C)C)C(C)C.[Cl-].[NH2:26][NH2:27]>CS(C)=O.CO>[N:11]1([C:2]2[C:7]([F:8])=[C:6]([NH:26][NH2:27])[N:5]=[C:4]([CH3:10])[N:3]=2)[CH2:15][CH:14]=[CH:13][CH2:12]14,6-Dichloro-5-fluoro-2-methylpyrimidine (181 mg, 1.0 mmol) was dissolved in 4 mL of DMSO and stirred at room temperature. 3-Pyrroline (71 mg, 1.05 mmol) was added, followed by DIPEA (244 μL, 1.4 mmol). The resulting reaction mixture was stirred until displacement of the first chloride was complete, and then hydrazine (350 μL) and MeOH (˜2 mL) were added to the reaction mixture. The contents were then heated to 70° C. for 2 h, until displacement of the second chloride was complete. The reaction mixture was then cooled to room temperature and purified by RP-HPLC to provide 4-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-6-hydrazino-2-methylpyrimidine (142 mg, 68%).
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