Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., name: 3-Methyl-4-nitro-1H-pyrazole
Procedure B:General Procedure for the Synthesis of 4-Amino-3 -methyl- 1-N-alkylated pyrazolesA solution of 3-methylpyrazole (1.96mL, 24.0mmol) in sulfuric acid (15mL) was cooled to – 5C and potassium nitrate (l . leq) was added portion-wise. The reaction was warmed to rt and stirred for 16h. The mixture was cooled to 0C and neutralized with ammonium hydroxide solution. The resulting solid was filtered and air-dried to give 3-methyl-4-nitro- 1H-pyrazole. To a solution of 3-methyl-4-nitropyrazole (300mg, 2.6mmol), potassium carbonate (2eq) and the alkylating reagent (l. leq) in acetonitrile (lOmL) was heated at 60C for 18h. After cooling to rt the mixture was diluted with EtOAc and washed with water. The organic phase was collected, dried (MgSC^) and concentrated in vacuo. The crude residue was dissolved in methanol (lOmL), palladium on carbon (50mg) was added and the reaction was stirred under a balloon of hydrogen for 18h. The resulting mixture was filtered through Celite and the filtrate concentrated in vacuo to give the desired product.Example 23: 2-((6-(l-(2-methoxyethyl)-3 -methyl- 1 H-pyrazo 1-4-ylamino)- 1 H-pyrazo lo [3,4- d]pyrimidin- 1 -yl)methyl)benzonitrileThe following compound was made according to the procedure in Example 1, using l-(2- methoxyethyl)-3 -methyl- lH-pyrazo 1-4-amine. 1 -(2 -methoxyethyl)-3 -methyl- lH-pyrazo 1-4- amine was prepared by Procedure B using l-bromo-2-methoxyethane as alkylating agent:1H NMR (d6-DMSO) delta 9.29-9.36 (m, 1Eta), 8.94 (s, 1Eta), 8.09 (s, 1Eta), 7.89 (d, 1Eta), 7.65 (td, 1Eta), 7.51 (t, 1Eta), 7.28-7.30 (m, 1Eta), 5.68 (s, 2Eta), 4.15 (t, 2Eta), 3.63 (t, 2Eta), 3.18 (s, 3Eta), 2.14 (s, 3H); LC-MS method B, (ES+) 389.1, RT = 7.86min
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; CELLZOME LIMITED; RAMSDEN, Nigel; HARRISON, Richard John; OXENFORD, Sally; BELL, Kathryn; PITON, Nelly; DAGOSTIN, Claudio; BOUSSARD, Cyrille; RATCLIFFE, Andrew; WO2011/48082; (2011); A1;,
Pyrazole – Wikipedia,
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