5-chloro-1-Methyl-4-nitro-1H-pyrazole

7-(Azetidin-l-yl)-3-methyl-l-(l-methyl-5-(4-(trifluoromethyl)phenyl)-lH- pyrazol-4-yl)-lH-pyrazolo[4, -d]pyrimidine (a) 5-Chloro-l-methyl-4-nitro-lH-pyrazole Lithium bis(trimethylsilyl)amide (1.0 M, 65 mL, 65 mmol) in THF is added dropwise into a solution of l-methyl-4-nitro-lH-pyrazole (5.50 g, 43.3 mmol) and hexachloroethane (10.54 g, 44.5 mmol) in methylene chloride (120 mL) at 25 °C. The reaction mixture is stirred at 25 °C for 60 min, and then quenched with water (1 mL). The mixture is evaperated to dryness. The residue is washed with water (50 mL), sat. NaHCC>3 two times (2x30 mL) and brine (30 mL) successively, and then dried under vacuum to give 6.50 g of product (93percent yield). MS (ESI) mJz 162.0 [M+H]Step B. 1-Methyl-4-nitro-1H-pyrazole (1 g, 7.87 mmol) was dissolved in 12 mL of dry THF.Cool to -78 ° C under a nitrogen atmosphere, and slowly add 6 mL of LDA at a concentration of 2 mol/L.Stirring was continued for 1 h at -78 ° C under a nitrogen atmosphere;Hexachloroethane (2.42 g, 10.2 mmol) was dissolved in 12 mL of anhydrous THF and slowly added dropwise to the above reaction mixture.Stir at -78 °C for 2 h, then warm to room temperature and continue stirring for 1 h, then quenched with saturated aqueous ammonium chloride.The organic phase was washed with an aqueous solution of ammonium chloride (20 mL×1) and ethyl acetate (10 mL×3).The combined organic layers were dried with anhydrous sodium sSeparated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3:1).1-Methyl-4-nitro-5-chloro-1H-pyrazole (691 mg, 54percent) was obtained as a yellow solid.Example 15-chloro-1-methyl-4-nitro-1H-pyrazole [0177] 4-nitro-1-H-pyrazole (5 g, 44.2 mmol) was added sodium hydroxide (1M, 200 mL) and dimethyl sulfate (31 mL, 330 mmol). The mixture was stirred at room temperature for 72 h and the mixture was extracted with CHTo a 500 mL round bottom flask containing 4-nitro-i-H-pyrazole (5g, 44.2 mmol) was added sodium hydroxide (1M, 200 mL) and dimethyl sulfate (31 mL, 330 mmol). The mixture was stirred at room temperature for 72 h and the mixture was extracted with CH

Molecular Weight:161.55
XLogP3:1
Hydrogen Bond Acceptor Count:3
Exact Mass:160.9992041
Monoisotopic Mass:160.9992041
Topological Polar Surface Area:63.6
Heavy Atom Count:10
Complexity:148
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes