Category: 28466-21-9

Some common heterocyclic compound, 28466-21-9, name is 1,3,5-Trimethyl-1H-pyrazol-4-amine, molecular formula is C6H11N3, 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. Recommanded Product: 28466-21-9

Step A (1,3,5-trimethyl-pyrazol-4-yl)-isothiocyanate A mixture of 4-amino-1,3,5-trimethylpyrazole (1.32 g, 10.6 mmol) in 50 mL each of CHCl3 and saturated aqueous NaHCO3 was treated dropwise with thiophosgene (0.812 mL, 10.6 mmol) and stirred vigorously for 20 minutes. The layers were separated and the organic phase was washed with brine. After drying (Na2 SO4), the solvent was evaporated in vacuo to provide the title compound (1.8 g, brown oil) suitable for use directly in the next step. NMR (DMSO-d6, 300 MHz): 2.12 (s, 3H, ArCH3), 2.22 (s, 3H, ArCH3), 3.63 (s, 3H, NHCH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28466-21-9, its application will become more common.

Reference:
Patent; American Home Products Corporation; US6011053; (2000); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 28466-21-9, name is 1,3,5-Trimethyl-1H-pyrazol-4-amine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H11N3

Reference Example 37 Ethyl 4-{4-chloro-7-(1-ethylpropyl)-2-[(1,3,5-trimethyl-1H-pyrazol-4-yl)amino]-1H-benzimidazol-1-yl}butanoate A mixture of ethyl 4-[2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (Reference Example 33; 371 mg, 1.00 mmol), 4-amino-1,3,5-trimethylpyrazole (375 mg, 3.00 mmol) and p-toluenesulfonic acid monohydrate (190 mg, 1.00 mmol) in 1-methyl-2-pyrrolidinone (3 mL) was stirred at 150 C. for 16 hr. After cooling, aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. Organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluding with a 0-5% methanol/ethyl acetate gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound (340 mg, 0.74 mmol, 74%) as a colorless solid. mp 177-178 C. 1H NMR (CDCl3) delta 0.86 (t, J=7.3 Hz, 6H), 1.28 (t, J=7.0 Hz, 3H), 1.64-1.85 (m, 4H), 2.03-2.16 (m, 2H), 2.20 (s, 3H), 2.22 (s, 3H), 2.44-2.51 (m, 2H), 2.87-2.99 (m, 1H), 3.74 (s, 3H), 4.10-4.24 (m, 4H), 6.79 (d, J=8.3 Hz, 1H), 6.90 (s, 1H), 7.08 (d, J=8.3 Hz, 1H). MS Calcd.: 459; Found: 460 (M+H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 28466-21-9.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/186879; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics