5-Chloro-2-iodopyrimidine

In a 250 mL round bottom flask, 5-chloro-2-iodo-pyrimidine (15 mmol), 9-H carbazole (15 mmol), cuprous oxide (40 mmol), and DMAC (20 mL) were refluxed for 48 hours under an argon atmosphere. The obtained intermediate was cooled to room temperature, added to water, and then filtered through a pad of celite. The filtrate was extracted with dichloromethane, then washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated. The crude product gave the intermediate product P32-1To a stirred solution of Intermediate 2 (0.14 g, 0.51 mmol) in i-propyl alcohol (5 mL), TEA (0.22 g, 2.20 mmol) and 2-iodo-5-chloro-pyrimidine (0.1 g, 0.415 mmol) were added and the reaction mixture was heated in a microwave at 140 C for 40 min. The reaction mixture was cooled down to rt and concentrated under vacuum. The resulting crude product was purified by flash chromatography to afford the title compound. Yield: 60% (83.46 mg, pale brown oil). 1H NMR (400 MHz, CDCl3): delta 8.47 (s, 2H), 6.89 (d, J = 1.6 Hz, 1H), 6.83 (d, J = 8.0 Hz, 1H), 6.74 (d, J = 8.0 Hz, 1H), 5.99 (s, 2H), 3.66-3.64 (m, 4H), 3.37-3.35 (m, 1H), 2.44-2.38 (m, 2H) 2.35-2.30(m, 2H), 1.27 (d, J = 6.4 Hz, 3H). LCMS: (Method A) 439.0 (M+H), Rt. 3.40 min, 98.3% (Max). HPLC: (Method A) Rt. 3.43 min, 98.6% (Max).Exampie 44: [1-Benzyl-3-(5-chloro-py rimidin-2-y1)-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl](1, 1-dioxo-[1, 4]thiazinan-4-yl)-methanone44a): Ethyl 1-benzyl-3-(5-chloropyrimidin-2-yl)-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate A flask was charged with ethyl1-benzyl-4-methyl-3-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-5-(tri fluoromethyl)-1H-pyrrole-2-carboxylate [see 41d)] (947 mg, 2.1 mmol), Cs2C03 (2.14 g, 6.50 mmol), 5- chloro-2-iodopyrimidine (781 mg, 3.2 mmol), DME (16 mL) and H20 (4 mL). The suspension was purged with Ar for 50 min before PdCI2 (dppf) (158 mg, 0.2 mmol) was added. The reaction mixture was stirred at 95C for 2 h. The reaction mixture was cooled and filtered over celite and washed with DCM (30 mL). The filtrate was concentrated in vacuo and purified by flash CC (silica, gradient heptane/EtOAc, 1:0 9:1) to give the desired product 412 mg (45%) as a colourless oil.A reaction mixture of methyl 4-((4, 4, 4-trifluoro-1-(2-methyl-4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)phenyl)butyl)amino)benzoate (7.85 g) obtained in Example 1, step F,

Molecular Weight:240.43
XLogP3:1.5
Hydrogen Bond Acceptor Count:2
Exact Mass:239.89512
Monoisotopic Mass:239.89512
Topological Polar Surface Area:25.8
Heavy Atom Count:8
Complexity:72.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes