Category: 25016-09-5

Synthetic Route of 25016-09-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 25016-09-5 name is 1,3-Dimethyl-1H-pyrazole-5-carbaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

1 Preparation of 2-pyridyl-(1,3-dimethyl-5-pyrazolyl)methanol: 300 ml of dry tetrahydrofuran solution containing 5.5 g of 2-bromopyridine was cooled to -78C, and 5.45 g of n-butyl lithium hexane solution (15 w/w %) was dropwise added thereto and stirred for 30 minutes. Then, 4.2 g of 1,3-dimethyl-5-formylpyrazole was dropwise added thereto. Afterwards, this was gradually heated up to room temperature and stirred for 15 hours. The solution was neutralized by adding 2 N hydrochloric acid thereto, and then extracted three times each with 150 ml of ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (developing solution; chloroform) to give 5.2 g of 2-pyridyl-(1,3-dimethyl-5-pyrazolyl)methanol as a brown oily product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dimethyl-1H-pyrazole-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LIMITED; EP556396; (1993); A1;,
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. 25016-09-5, name is 1,3-Dimethyl-1H-pyrazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 25016-09-5

Step 3: Preparation of 3-(2,5-dimethyl-2H-pyrazole-3yl)-2-(4-fluoro phenyl) acrylic acid (16) A mixture of compound 15 (1 gram, 8.0 mmol) and 4-fluorophenyl acetic acid (1.24 grams, 8.0 mmol), acetic anhydride (2 mL) and triethylamine (0.84 mL, 6.0 mmol) was refluxed under nitrogen atmosphere for 5-6 h. The excess of acetic anhydride was distilled out at the same temperature. The mixture was then diluted with water (100 mL) and neutralized with 2N hydrochloric acid. The solid precipitated was filtered and dried under vacuum to afford the title compound 3-(2,5-dimethyl-2H-pyrazole-3yl)-2-(4-fluoro phenyl) acrylic acid (16) 1.4 gram as a pale brown solid. Yield: 67%; 1H NMR (200 MHz, DMSO-d6): delta 12.75 (s, D2O exchangeable) 7.66 (s, 1H), 7.26-7.12 (m, 4H), 5.0 (s, H) 3.84 (s, 3H), 2.05 (s, 3H); Mass (CI method, i-butane): 261 (M+1, 80%); IR: numax (KBr, cm-1): 3440, 1695.

According to the analysis of related databases, 25016-09-5, the application of this compound in the production field has become more and more popular.

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. 25016-09-5, name is 1,3-Dimethyl-1H-pyrazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H8N2O

151. (+)-2- 3,4-trans)-l-gi,3-dimethyl-lH-pyrazol-5-yl)methyl)-4- methylpyrrolidin-3-yl)-7-ftetrahydro-2H-pyran-4-yl)imidazo[5,l- 1 [l,2,41triazin- 4(3H)-one [1110] To a stirred solution of (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l- J[l,2,4]triazin-4(3H)-one (80 mg, 0.26 mmol) in MeOH (10 mL) was added l,3-dimethyl-lH-pyrazole-5-carbaldehyde (39.2 mg, 0.31 mmol) at room temperature and stirred for 2 h under argon atmosphere. To the resulting solution was added NaCNBH3 (49.9 mg, 0.74 mmol) and stirring was continued for another 8 h at room temperature. The volatiles were evaporated under reduced pressure. The residue was diluted with water and extracted with CH2CI2 (2 x 20 mL). Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford (+)-2-((3,4-trans)-l-((l,3-dimethyl-lH- pyrazol-5-yl)methyl)-4-methylpyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4- yl)imidazo[5,l- J[l,2,4]triazin-4(3H)-one (40 mg, 37%) as an off-white solid; 1H- NMR (DMSO-d6, 400 MHz): delta 11.65 (bs, 1H), 7.62 (s, 1H), 5.89 (s, 1H), 3.96-3.91 (m, 2H), 3.67 (s, 3H), 3.59 (s, 2H), 3.50-3.47 (m, 2H), 3.41-3.39 (m, 1H), 2.94-2.85 (m, 2H), 2.81-2.79 (m, 2H), 2.65-2.61 (m, 1H), 2.25-2.24 (m, 1H), 2.14 (s, 3H), 1.89- 1.82 (m, 4H), 1.09 (d, 3H); Mass (ESI): 412.3 [M++l]; LC-MS: 98.59%; 412 (M++l); (column; X-bridge C-18, (50×3.0 mm, 3.5mu); RT 1.74 min. 0.05% TFA in water: ACN; 0.8 ml/min); UPLC (purity): 99.67%; (column; Acquity BEH C-18, 50×2.1 mm, 1.7mu; RT 1.18 min. 0.025% TFA (Aq): ACN; 0.50 ml/min.; Chiral HPLC: 98.34%, R,= 11.21 min (Chiralpak IA, 250 x 4.6mm, 5mu; mobile phase (A) 0.1% DEA in n-Hexane (B) DCM:MeOH (80:20) (A: B : 80:20); flow Rate: 1.00 mL/min); Optical rotation [a]D2: + 21.85 (c = 0.25, DCM); TLC: 5% MeOH/DCM (Rf: 0.5).

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 25016-09-5.