50 μL (0.680 mmol, 1.3 equiv) thionyl chloride were added to a room temperature solution of 135 mg (0.523 mmol, 1.0 equiv) 1-cyclopentyl-3-ethyl-1h-indazole-6-carboxylic acid and 10 μL DMF in 5 mL anhydrous toluene. The reaction mixture was heated to reflux for 2 hours, then cooled to room temperature, concentrated to dryness on a rotary evaporator, and dried at high vacuum, room temperature for several hours. 21 mg (0.523 mmol, 1.0 equiv) sodium hydride, 60% oil dispersion, were added to a separate flask containing a room temperature solution of 86 mg (0.523 mmol, 1.0 equiv) 5-amino-4,6-dichloro-pyrimidine in 5 mL anhydrous DMF. After 10 minutes, a solution of the acid chloride (prepared above) in 5 mL anhydrous DMF was added, and the mixture stirred for 24 hours at room temperature. The reaction mixture was then heated to 70° C. for 1.5 hours, cooled to room temperature, diluted with 75 mL ethyl acetate, washed 2×15 mL H2O, 1×16 mL brine, and dried over MgSO4. The crude product was purified on a silica gel column (20 % ethyl acetate/hexanes) to give 31 mg (15%) of white crystalline solid: mp 171-172° C.; Anal. calcd for C19H19N5OCl2: C, 56.44; H, 4.74; N, 17.32. Found: C, 56.38; H, 4.76; N, 17.33.
