Lithium Hexamethyldisilazide → N'-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloro-2-pyridinyl)amino)-2-chloro-3-pyridinyl)-N,N-dimethylsulfamide

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To a 100-mL round-bottomed flask was added 4-(5-chloro-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (Example 356, Step 1; 960 mg, 4.01 mmol), N′-(5-amino-2-chloro-3-pyridinyl)-N,N-dimethylsulfamide (1004 mg, 4.01 mmol) and lithium bis(trimethylsilyl)amide (Aldrich; 3352 mg, 20.03 mmol) in tetrahydrofuran (20 mL) at 0° C. After the addition, the reaction mixture was stirred at 0° C. for 20 min. The reaction mixture was diluted with satd NH4Cl (30 mL) and extracted with CH2Cl2 (3×200 mL). The organic extract was washed with satd NaCl (30 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a yellow solid. The crude product was purified by silica gel chromatography eluting with 5% MeOH/CH2Cl2 to give N′-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloro-2-pyridinyl)amino)-2-chloro-3-pyridinyl)-N,N-dimethylsulfamide (1.29 g, 2.74 mmol, 68.5% yield) as a yellow solid. m/z (ESI, +ve ion) 470.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 2.61 (s, 3H) 2.95 (s, 6H) 5.48 (br. s., 2H) 6.80 (s, 1H) 8.31 (d, J=2.74 Hz, 1H) 8.38 (d, J=2.54 Hz, 1H) 8.74 (d, J=2.54 Hz, 1H) 8.85 (d, J=2.74 Hz, 1H) 12.35 (s, 1H).

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