Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 2-(benzyloxymethyl)-4-hydroxy-N-(naphthalen-2-ylmethyl)pyrimidine-5-carboxamide

To a stirred suspension of compound 2-e (5 g, 19.2 mmol) in DMF (50 mL) was added HATU (8.04 g, 21.1 mmol) and EIPEA (2.73 g, 21.1 mmol). The reaction mixture was stirred at ambient temperature until all dissolved. To this stirred solution was added compound 2-22-a (3.17 g, 20.2 mmol) in DMF (20 mL) via syringe. The solution was stirred at room temperature overnight. The reaction mixture was poured into ice-water and extracted with DCM and then concentrated to give a residue. The residue was purified by column chromatography with the eluent DCM:MeOH=60:1 to afford product, 2-22-b, (5.2 g, 68%). 1H NMR (300 MHz, CDCl3): δ 9.38 (s, 1H), 8.90 (s, 1H), 7.81-7.75 (m, 4H), 7.43-7.34 (m, 8H), 4.77 (d, J=6.0 Hz, 2H), 4.67 (s, 2H), 4.56 (s, 2H). LC-MS: (M+H)+ 400.