Category: 687635-04-7

These common heterocyclic compound, 687635-04-7, name is (3-(1H-Pyrazol-1-yl)phenyl)methanamine, its 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. Safety of (3-(1H-Pyrazol-1-yl)phenyl)methanamine

To 3-pyrazol-1-yl-benzylamine (0.5 mmol) in THF (2 mL) at room temperature were added Iso-butylaldehyde (0.6 mmol) and anhydrous magnesium sulfate (60 mg). After stirring for 1.5 h at room temperature, sodium borohydride (0.5 mmol) was added and the mixture stirred for a further 2 h. Water (3 ml) was added to the mixture and stirring resumed for 10 min. Additional water was added (1 ml) and the mixture was extracted with CH2Cl2 (10 mL*3). After being dried over anhydrous magnesium sulfate the solvent was removed under reduced pressure to give the crude product. This material was used in subsequent steps without further purification.

The synthetic route of (3-(1H-Pyrazol-1-yl)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dykes, Graeme James; Fletcher, Stephen Robert; Menet, Christel Jeanne Marie; Merayo, Nuria Merayo; Schmitt, Benoit Antoine; US2008/242661; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 687635-04-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 687635-04-7 as follows.

A solution of sodium hydrogen carbonate(0.364 g, 4.33 mmol) in H2O (3 ml) was slowly added to a stirredsolution of (3-(1H-pyrazol-1-yl)phenyl)methanamine sulfate (0.47 g, 1.73 mmol)in dichloromethane (8 ml) at 0C. A solution of cyanogen bromide (0.148 g, 4.52 mmol)in dichloromethane (3 ml) was then added to the reaction mixture at 0C. The mixturewas stirred at 0C for 30 minutes, allowed to come to ambient temperature andstirred for an additional 2 hours. The layers were separated, the dichloromethane extractwas washed with saturated sodium hydrogen carbonate solution (25 mL), saturatedsodium chloride solution (25 mL), dried over MgSO4 and evaporated in vacuoto a residue. The crude product was purified by flash silica chromatography,elution 20% ethyl acetate in heptane to give N-(3-(1H-pyrazol-1-yl)benzyl)cyanamide (0.261 g, 76%) as a whitesolid.1H NMR (400MHz, CDCl3) delta 7.93 (d, J = 2.5 Hz, 1H), 7.68 – 7.74 (m, 2H),7.62 (ddd, J = 8.1, 2.1, 0.8 Hz, 1H), 7.46 (t, J = 7.9 Hz, 1H),7.24 – 7.3 (m, 1H), 6.26 – 6.64 (m, 1H), 4.35 (s, 1H), 4.29 (d, J = 4.5Hz, 2H).

According to the analysis of related databases, 687635-04-7, the application of this compound in the production field has become more and more popular.

Electric Literature of 687635-04-7,Some common heterocyclic compound, 687635-04-7, name is (3-(1H-Pyrazol-1-yl)phenyl)methanamine, molecular formula is C10H11N3, 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.

To pyrazol- 1 -ylbenzylamine (0.5 mmol) in tetrahydrofuran (2 mL) at room temperature are added cyclopropylmethylaldehyde (0.6 mmol) and anhydrous magnesium sulfate (60 mg). After stirring for 1.5h at room temperature, sodium borohydride (0.5 mmol) is added and the mixture is then stirred for a further 2h. Water (3 mL) is added to the mixture and stirring resumes for 1 Omin. Additional water is added (1 mL) and the mixture is extracted with dichloromethane (10 mL x 3). After being dried over anhydrous magnesium sulfate the solvent is removed under reduced pressure to give the crude product. This material may be used in subsequent steps without further purification. [0290] The amine obtained using the methods described in the previous step (0.26 mmol) is added to a solution of chloro-l-methyl-3-tert-butyl-l,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one (0.13 mmol) in t-BuOH (0.5 mL). The reaction is heated in a sealed tube to 1000C for 24h. On complete reaction (monitored by LCMS), the mixture is allowed to cool to room temperature and the solvent is then removed under reduced pressure. The final compound may be isolated by preparative HPLC. [0291] Preparative HPLC: Waters XBridge Prep C 18 5mum ODB 19mm ID x 100mm L. The method uses MeCN/H2O 65-90% gradients. H2O contains 0.1% Trifluoroacetic acid (TFA)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-(1H-Pyrazol-1-yl)phenyl)methanamine, its application will become more common.