Cl[C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[C:4]([CH3:10])[N:3]=1.[S:11]1[CH:15]=[CH:14][N:13]=[C:12]1[CH2:16][NH2:17].C(N(CC)CC)C.[NH2:25][NH2:26]>CS(C)=O>[F:8][C:7]1[C:2]([NH:25][NH2:26])=[N:3][C:4]([CH3:10])=[N:5][C:6]=1[NH:17][CH2:16][C:12]1[S:11][CH:15]=[CH:14][N:13]=14,6-Dichloro-5-fluoro-2-methylpyrimidine (180 mg, 1 mmol) was dissolved in 1 mL of DMSO and stirred at room temperature. (1,3-Thiazol-2-ylmethyl)amine (124 mg, 1.1 mmol) was added, followed by triethylamine (150 μL, 1.1 mmol). The resulting reaction mixture was stirred for 3 h, then hydrazine was added (1.0 mL), and the contents were heated to 60° C. for 1.5 h. The reaction mixture was then cooled to room temperature and purified by RP-HPLC to provide 5-fluoro-4-hydrazino-2-methyl-6-[(1,3-thiazol-2-ylmethyl)amino]pyrimidine (97 mg, 38%). LCMS: (M+H)+: 255.2.
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