A mixture of (R)-2-(3-aminopyridin-4-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 91, 1 eq), benzoic acid (3 eq), HATU (3 eq), and DIPEA (4 eq) in dry THF under Ar was stirred at 90° C. for 18 h. The mixture was cooled to rt and water was added and extracted with EtOAc. The organic layer was dried with Na2SO4, concentrated and the residue was purified by silica gel column to give the title compound. LCMS (0.05% TFA): 457.2 m/z (M+H)+; 1H-NMR (DMSO-d6, 500 MHz): δ: 13.75 (s, 1H), 10.00 (bs, 1H), 8.55 (bs, 1H), 8.39 (d, 1H, J=5.0 Hz), 8.31 (s, 1H), 8.07 (m, 2H), 7.69 (m, 3H), 4.46 (m, 1H), 4.39 (m, 1H), 3.38 (s, 3H), 2.02-1.63 (m, 10H), 0.77 (t, 3H, J=7.5 Hz).
