Category: 72788-94-4

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. 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 72788-94-4

Triethylamine (4.17 mL, 3.0 mmol) and mesyl chloride (1.57 mL, 2.00 mmol) were added to a solution of (5-chloro-2-pyrazinyl)methanol (1.44 g, 10.0 mmol) in anhydrous THF (20 mL) at 00C. The mixture was stirred at 00C for 0.5 h then partitioned between EtO Ac/water. The organic fraction was dried (MgSO4) and the solvent was removed under reduced pressure to give the crude mesylate. The mesylate was dissolved in acetone (40 mL), sodium iodide (7.5 g, 50 mmol) was added and the mixture was refluxed for Ih. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc/water. The residue was chromatographed on silica gel (DCM) to give 2- chloro-5-(iodomethyl)pyrazine. Sodium hydride (60% w/w, 0.36 g, 9.0 mmol) was added to a solution of(S)-2-nitro-6,7-dihydro-5H-imidazo[2,l-b][l,3]oxa-zin-6-ol (0.93 g, 5.02 mmol) and 2-chloro-5-(iodomethyl)pyrazine (1.54 g, 6.05 mmol) in DMF (10 mL) at -78C. The mixture was stirred at 00C for 1 h and then quenched with ice. EtOAc (200 mL) was added, the organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with a gradient (0-5%) MeOH/EtOAc to give the title compound (1.015 g, 65%) as a white solid. APCI MS m/z 312.6 (M + H). 1H NMR (400 MHz, (CD3)2SO) delta 8.76 (d, J= 1.4 Hz, IH), 8.50 (d, J= 1.4 Hz, IH), 8.02 (s, IH), 4.85 (d, J = 13.7 Hz, IH), 4.81 (d, J= 13.7 Hz, IH), 4.70 (td, J= 12.1, 2.6 Hz, IH), 4.49 (bd, J= 12.0 Hz, IH), 4.29-4.38 (m, 2H), 4.25 (dd, J= 13.5, 3.3 Hz, IH).

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 72788-94-4.

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; WO2009/120789; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 72788-94-4,Some common heterocyclic compound, 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine, molecular formula is C5H5ClN2O, 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 a solution of Intermediate 112A (2.00 g, 13.84 mmol) in CHCl3 (20 mL) was added active manganese dioxide (4.81 g, 55.3 mmol) and the resulting suspension was refluxed for 2 h. The reaction mixture was cooled to ambient temperature, filtered through Celite and washed with CHCl3 (200 mL). The combined filtrates were washed with brine (200 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Redisep-24 g, 20-30 % EtOAc/ n-hexane) to obtain Intermediate 112B (1.00 g, 50.70%) as a white solid.1H NMR (400 MHz, DMSO-d6) delta ppm 8.98 (d, J = 1.51 Hz, 1 H), 9.04 (d, J = 1.51 Hz, 1 H), 10.07 (s, 1 H). LCMS: The compound did not ionize well.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5-(hydroxymethyl)pyrazine, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 72788-94-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

D. Synthesis of (6S)-2-nitro-6-({5-[4-(trifluoromethoxy)phenyl]-2-pyrazinyl}methoxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (4) by the method of Scheme 3 Et3N (4.17 mL, 29.9 mmol) and mesyl chloride (1.57 mL, 20.3 mmol) were added to a solution of (5-chloro-2-pyrazinyl)methanol (45) (obtained by chlorination and reduction of 5-hydroxypyrazine-2-carboxylic acid, as reported by Kiener et al., 1994) (1.443 g, 9.98 mmol) in anhydrous THF (20 mL) at 0 C. The mixture was stirred at 0 C. for 0.5 h, then partitioned between EtOAc and water. The organic fraction was dried (MgSO4) and the solvent was removed under reduced pressure to give the crude mesylate. The mesylate was dissolved in acetone (40 mL), sodium iodide (7.5 g, 50 mmol) was added, and the mixture was refluxed for 1 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and water. The organic fraction was concentrated under reduced pressure and the residue was chromatographed on silica gel (eluting with CH2Cl2) to give 2-chloro-5-(iodomethyl)pyrazine (46) (1.54 g, 61%), which was used immediately due to its instability.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Chloro-5-(hydroxymethyl)pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Global Alliance for TB Drug Development; US2012/28973; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C5H5ClN2O

Preparation 299; To a solution of (5-chloro-2-pyrazinyl)methanol (11.0 g) in dioxane(110 mL) was added manganese (IV) oxide (26.5 g) and (carbethoxymethylene)triphenylphosphorane (29.2 g). After stirring for 2 hours at room temperature, a resulting precipitate was filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E) -3-(5-chloro-2-pyrazinyl)acrylate (11.0 g).^-NMR (300 MHz, CDC13) 8 1.35 (3H, t, J = 7 Hz), 4.30 (2H, q, J = 7 Hz), 7.01 (1H, d, J = 15 Hz), 7.66 (1H, d, J = 15 Hz), 8.43 (1H, s), 8.60 (1H, s)

The synthetic route of 72788-94-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2006/16680; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem