Category: 105250-17-7

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.105250-17-7, name is (2-Aminopyridin-4-yl)methanol, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.name: (2-Aminopyridin-4-yl)methanol

Intermediate C: 1 -(4-((2-aminopyridin-4-yl)methoxy)naphthalen-1 -yl)-3-(3-ferf-butyl-1 -p- tolyl-1 H-pyrazol-5-yl)urea To a solution of 4-nitronaphthol (5.17 g, 27.3 mmol), triphenylphosphine (10.75 g, 41 .0 mmol) and 2-aminopyridine-4-methanol (5.09g, 41.0 mmol) in THF (50 mL) at -15°C was added dropwise DIAD (8.07 mL, 41.0 mmol) and the mixture then allowed to warm to RT and stirred overnight. The volatiles were removed in vacuo and the residue was triturated with EtOAc (150 mL), and the crude product was collected by filtration and washed with EtOAc (100 mL). A second trituration with MeOH (100 mL) gave 2-amino-4-((4-nitronaphthalen-1 – yloxy)methyl)pyridine (4.54 g, 56percent) as a yellow solid: m/z 296 (M+H)+ (ES+).A solution of 2-amino-4-((4-nitronaphthalen-1 -yloxy)methyl)pyridine (4.50 g, 15.24 mmol) in MeOH (200 mL) and AcOH (200 mL) was passed through a Thales H-cube (2.0 mLmin”1, 40 °C, 55 mm 10percent Pt/C Cat-Cart, full hydrogen mode) and the volatiles were removed in vacuo. The crude product was subjected to SCX capture and release and the solvent was removed in vacuo to give 2-amino-4-((4-aminonaphthalen-1 -yloxy)methyl)pyridine, (3.82g, 94percent) as a purple solid: m/z 266 (M+H)+ (ES+). A solution of CDI (4.18 g, 25.8 mmol) in DCM (15 mL) was added dropwise under nitrogen to a solution of Intermediate A (5.91 g, 25.8 mmol) in DCM (15 mL) over 40 min. The resulting solution was stirred at RT for 1 hr and was then added dropwise under nitrogen to a solution of 2-amino-4-((4-aminonaphthalen-1 -yloxy)methyl)pyridine (3.80 g, 12.9 mmol) in DCM and the mixture was stirred overnight. The volatiles were removed in vacuo.and the residue was purified by flash column chromatography (Si02, 120 g, MeOH in DCM, 0-6percent, gradient elution) to give the tite compound, Intermediate C, as an off white solid (4.27 g, 63percent): m/z 521 (M+H)+ (ES+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105250-17-7, (2-Aminopyridin-4-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; RESPIVERT LIMITED; KING-UNDERWOOD, John; ITO, Kazuhiro; STRONG, Peter; RAPEPORT, William Garth; CHARRON, Catherine Elisabeth; MURRAY, Peter John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart Thomas; WO2011/124923; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 105250-17-7, 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. 105250-17-7, name is (2-Aminopyridin-4-yl)methanol, molecular formula is C6H8N2O, The 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.

Preparation of 4-({rtgrt-butvirdimethyl)silylloxy}methvDpyridin-2-amineA solution of (2-aminopyridin-4-yl)methanol (5.0 g, 40 mmol), tert- butyldimethylsilyl chloride (6.07 g, 40 mmol), N-ethyl-N-isopropylpropan-2-amine (7.0 mL, 40 mmol) and ??N-dimethylpyridin-4-amine (0.49 g, 4 mmol) in dichloromethane (50 mL) was stirred 2 days at ambient temperature under nitrogen. The resulting reaction mixture was washed in sequence with aqueous sodium hydroxide (1 N), water and brine. It was then dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel using 50 percent ethyl acetate in hexane to yield pure title compound (5.47 g).1H NMR (300 MHz, CD3CN) ? 7.75 (m, IH), 6.39 -6.48 (m, 2H), 4.70 (bs, IH), 4. 50 (s, 2H), 0.83 (s, 9H) and 0.03 ppm (s, 6H); ES-MS m/z 239.3 [M+H]+, HPLC RT (min) 2.35.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 105250-17-7, (2-Aminopyridin-4-yl)methanol.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/133006; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 105250-17-7, name is (2-Aminopyridin-4-yl)methanol, molecular formula is C6H8N2O, The 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. Safety of (2-Aminopyridin-4-yl)methanol

To a stirred solution of 67 (1.39 g, 11.2 mmol) in EtOH (46.5 ml)-water (6.5 ml) was added NaHCO3 (1.88 g, 22.3 mmol), followed by a 50percent w/w aqueous solution of chloroacetaldehyde (2.84 ml, 1.75 g, 22.4 mmol). The resultant suspension was stirred and refluxed for 2 h. The dark amber-colored reaction mixture was carefully concentrated (frothing) under reduced pressure to approximately half its original volume and then filtered. Collected solid was washed with MeOH. Combined filtrate and washings were concentrated in vacuo and yielded a dark, oily two-phase mixture. Treatment with EtOH produced a mixture of solid precipitate and a homogeneous liquid phase, which was filtered. The filtrate was concentrated under reduced pressure to a dark oil, which was purified via flash chromatography on silica gel, eluting with CH2CI2-CH3OH -NH4OH (91.5:8.5:0.25), to obtain compound 68 as a pale yellow solid (1.34 g; 80percent). To a solution of 68 (1.20 g, 8.10 mmol) in MeOH (5 ml) was added acetone (48 ml). A small amount of dark precipitate formed and was removed by filtration (0.45 muM syringe filter). To the clear yellow filtrate was added via syringe 1 M ethereal HCI (8.1 ml, 8.1 mmol). The resultant mixture was stirred briefly and was then filtered. The hygroscopic solid thus isolated was washed rapidly with acetone and dried under vacuum at 50 0C to obtain the hydrochloride salt of 68 as a tan powder (1.34 g; 89percent). EPO

With the rapid development of chemical substances, we look forward to future research findings about 105250-17-7.

Reference:
Patent; SCHERING CORPORATION; WO2007/1975; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 105250-17-7 ,Some common heterocyclic compound, 105250-17-7, molecular formula is C6H8N2O, 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.

A mixture of (2-aminopyridin-4-yl)methanol (5.00 g, 40.3 mmol) and aqueous hydrobromic acid (50 mL, c =. 48 percent , 440 mmol) was heated at 100D for 24 hours. The mixture was cooled to room temperature and concentrated under reduced pressure. Ethyl acetate was added to the crude product and the resulting solid was filtered, washed with ethyl acetateand dried under reduced pressure to give 7.70 g (71 percent) of the title compound as a crude product that was used without further purification.LC-MS (Method 2): R = 0.68 mm; MS (ESIpos): m/z = 186; 188 [M+H]1H-NMR (400 MHz, d6-DMSO): oe [ppm] = 8.10 (brs, 2H), 7.90 (d, J = 6.9 Hz, IH), 6.98 (s,1 H), 6.84 (dd, J = 1.8 and 6.9 Hz, 1 H), 4.65 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,105250-17-7, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 105250-17-7, 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 105250-17-7 as follows.

To a solution of 4-nitronaphthalen-1-ol (2) (5.17 g, 27.3 mmol), PPh3 (10.75 g, 41.0 mmol) and 2-aminopyridine-4-methanol (1) (5.09 g, 41.0 mmol) in THF (50 mL) was added dropwise DIAD (8.07 mL, 41.0 mmol) at -15¡ã C.The mixture was stirred overnight at RT and the volatiles were removed in vacuo.The crude product was triturated from EtOAc (150 mL) and was collected by filtration and washed with EtOAc (100 mL).A second trituration from MeOH (100 mL) gave 2-amino-4-((4-nitronaphthalen-1-yloxy)methyl)pyridine (3) (4.54 g, 56percent) as a yellow solid: m/z 296 (M+H)+ (ES+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,105250-17-7, its application will become more common.

Reference:
Patent; Charron, Catherine Elisabeth; Fenton, Robert; Crowe, Scott; Ito, Kazuhiro; Strong, Peter; Rapeport, William Garth; Ray, Keith; US2012/244120; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem