Simple exploration of Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 110860-60-1, its application will become more common.

Some common heterocyclic compound, 110860-60-1, name is Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 110860-60-1

Synthesis of D-77; 1 g of compound (18) is added to 10 ml of phosphoric acid, and the mixture is heated to 30C to dissolve. This solution is cooled with ice and, while keeping the temperature of the solution at -5 to 0C, 0.46 g of sodium nitrite is added thereto, followed by stirring for 1 hour to obtain a diazonium salt solution. Separately, 0.93 g of the compound (17) is dissolved in 10 ml of methanol, and the aforesaid diazonium salt solution is added thereto at 8C or lower. At the time of completion of the addition, the ice bath is removed, followed by stirring the mixture for 2 hours. The reaction solution is added to 30 ml of acetonitrile, and the mixture is stirred at room temperature for 30 minutes. Crystals precipitated are collected by filtration, and spray-washed with 20 ml of acetonitrile. The crystals are added, without drying, to 50 ml of a 1% sodium hydrogencarbonate aqueous solution, and the mixture is stirred for 1 hour. The crystals are collected by filtration, and spray-washed with a sufficient amount of water. The thus-obtained crystals are added, without drying, to a solution composed of 15 ml of dimethylacetamide (DMAc) and 25 ml of water and, after stirring at 80C for 1 hour, the mixture is stirred at room temperature for 2 hours. Crystals precipitated are collected by filtration and spray-washed with 30 ml of a mixture of DMAc/water (=1/2). The thus-obtained crystals are dried to obtain 1.1 g of compound D-77 of the invention. Yield: 55.0%. Infrared absorption chart of compound D-77 is shown in Fig. 27. IR charts of typical compounds synthesized in Synthesis Examples 1 to 8 and those synthesized in the similar manner are shown in Figs. 1 to 27.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 110860-60-1, its application will become more common.

Reference:
Patent; FUJIFILM Corporation; EP2253674; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics