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A mixture of N-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-(1-(piperazin-1-yl)ethyl)pyridin-2-yl)benzo[d]thiazol-5-amine (0.300 g, 0.436 mmol) in dichloromethane (10 mL) was chilled to 0° C. in an ice bath, then triethylamine (0.304 mL, 2.181 mmol) was added to the mixture. After 10 min, dimethylcarbamic chloride (Aldrich; 0.141 g, 1.308 mmol) was added into the mixture dropwise via syringe. After the addition, the ice bath was removed and the mixture was allowed to stir under inert atmosphere overnight. The mixture was diluted with chloroform (20 mL) and water (10 mL). The organic layer was extracted with chloroform (3×10 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was adsorbed onto a plug of silica gel and purified by chromatography through a SiliCycle SiliaSep pre-packed silica-gel column (40 g), eluting with 20% MeOH in CH2Cl2 to give the urea as a tan oil. This material was diluted with trifluoroacetic acid (1.803 mL, 23.40 mmol) and stirred 5 min. Then trifluoromethanesulfonic acid (0.214 mL, 2.406 mmol) was added to the mixture. The reaction mixture was placed into a pre-heated (70° C.) bath and allowed to stir under inert atmosphere for 10 min. The heating bath was removed and the mixture was allowed to cool to ambient temperature. The mixture was concentrated in vacuo. The residue was diluted with dichloromethane (10 mL), then sodium carbonate (2.0 g) was added into the mixture with stirring. After 5 min, methanol (5 mL) was added into the mixture and allowed to stir 20 min. The mixture was filtered and concentrated in vacuo. The mixture was recrystallized from ethyl acetate/ethyl ether. This gave 4-(1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(benzo[d]thiazol-5-ylamino)pyridin-3-yl)ethyl)-N,N-dimethylpiperazine-1-carboxamide (0.070 g, 0.135 mmol, 61.7% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 12.24 (s, 1H) 9.36 (s, 1H) 8.92 (s, 1H) 8.92 (s, 1H) 8.37 (s, 1H) 7.91 (s, 1H) 8.05 (s, 1H) 7.83 (s, 2H) 3.53 (m, 1H) 3.10 (s, 4H) 2.70 (s, 6H) 2.43-2.55 (m, 3H) 2.36 (d, J=4.50 Hz, 4H) 1.38 (d, J=6.06 Hz, 3H). m/z (ESI, +ve ion) 519.1 (M+H)+.

1. additionAfter the addition
2. customthe ice bath was removed
3. additionThe mixture was diluted with chloroform (20 mL) and water (10 mL)
4. extractionThe organic layer was extracted with chloroform (3×10 mL)
5. dry with materialThe combined organic extracts were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. custompurified by chromatography through a SiliCycle SiliaSep pre-packed silica-gel column (40 g)
9. washeluting with 20% MeOH in CH2Cl2