Bergenin Since magnesium is added to dry THF The
flask wasSince magnesium is added to Bergenin dry THF. The flask was purged with argon and hermetically sealed with a rubber septum. The mixture was in a Heated oil bath for 15 min at 75 an embroidered by TLC showed the consumption of raw materials. The mixture was cooled and the residue was purified by flash chromatography to obtain 14 as a clear viscous acetylene oil: TLC Rf 0.39, 1 H-NMR δ 7.15, 6.80 6.72, 3800, 3797, 3.58, 2.20 , 13C δ 153, 6, 150.9, 125.6, 115.3, 111.9, 110.9, 81.7, 70.5, 55.8, 55.6, 19.3, IR 3290, 2999, 2833, 1593, 1499, 1220, 1049, HRFAB 183.1000. 2.4 diaminopyrimidine 5 for a bottle kiln dried 8 mL screw cap 2.4 iodopyrimidine added diamino-5 and CuI Pd2Cl2. Degassed anhydrous DMF was added, followed by 14 alkyne as L Solution in DMF.
Degassed anhydrous triethylamine was added and the mixture was again degassed using the freeze-thaw process pump. The vial was sealed under argon and heated at 50 for 1 hour. After cooling, the orange L Solution diluted with EtOAc and washed with a water / saturated Ttigter L NaHCO3 Solution and brine. The organic phase was dried over sodium sulfate and concentrated BMY 7378 to give the crude product which was purified by flash chromatography to give the coupled pyrimidine 15 as a pale solid. An analytical sample was produced by trituration in DCM. TLC Rf 0.61, mp decomposed above 180, 1H NMR δ 7.88, 7.05, 6.91, 6.79, 6.41, 6.22, 3.76, 3.73, 3.70 , 13C δ 163.8, 162.0, 158.5, 153.1, 150.6, 126.0, 115.3, 111.7, 111.5, 92.6, 90.5, 76.4 , 55, 8, 55.3, 20.2, 291.1442 HRFAB, HPLC tR 4.
71 min, 100%, Rt 8.27 min, 98.8%. Anal. C, H, N. 2.4 diamino 6th May methylpyrimidine for a bottle kiln dried 8 mL screw 2,4-diamino-6 iodine 5, CuI and Pd2Cl2 methylpyrimidine added. Degassed anhydrous DMF was added, followed by 14 alkyne as L Solution in DMF. Degassed anhydrous triethylamine was added and the mixture was again degassed using the freeze-thaw process pump. The vial was sealed under argon and heated at 50 for 2 hours. After cooling, the orange L Solution diluted with EtOAc and washed twice with water / saturated Ttigter L NaHCO3 Solution and brine. The organic phase was dried over sodium sulfate and concentrated to. Coupled the crude product which was purified by flash chromatography pyrimidine 16 as a white It give powder Rf 0.61, mp decomposed above 180, 1H NMR δ 7.07, 6.
92, 6.79, 6.28, 6.13, 3.77 3.76, 3.70, 2, 20, 13Cδ 166.8, 164.3, 160.9, 153.1, 150.6, 126.2, 115.0, 111.8, 111.5, 95.4, 88.7, 76, 5, 55 , 8, 55.3, 22.4, 20.5, 305.1591 HRFAB, HPLC tR 5.33 min, 98.6%, t R 8.92 min, 99.1%. 2.4 diamino 6th May ethylpyrimidine To an oven-dried 15 mL sealed R Hrchen 2.4 diamino-6-ethyl-5 iodopyrimidine, Pd2Cl2, CuI and acetylene 14 Date. Degassed anhydrous DMF and triethylamine was added and the tube was sealed and the mixture was degassed by freeze-drying, thawing pump. The mixture was stirred for 15 h at 50 and then. Into a separatory funnel with EtOAc The organic layer was washed twice with water / saturated Ttigter L NaHCO3 Solution and brine. The organic layer is then dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography to the coupled product 17 as a white It powder. An analytical sample was obtained by crystallization from MeCN. TLC Rf 0.61, mp decomposed above 180, 1H.