Category: 14160-93-1

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 14160-93-1, name is 4-Amino-6-chloropyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below., Formula: C5H4ClN3O

Compound 1.2 (249 mg, 1.58 mmol, 1 eq.) and 2,4,6- trimethoxybenzylamine (free-based by saturated sodium bicarbonate wash) (313 mg, 1.59 mmol, 1 eq.) were dissolved in dichloromethane (3 mL) at room temperature. Acetic acid (91 muL, 1.58 mmol, 1 eq.) was added and the reaction mixture was heated in a microwave at 100C for 5 minutes. Sodium triacetoxyborohydride (410 mg, 1.94 mmol, 1.2 eq.) was added at room temperature and the reaction was stirred overnight. Saturated sodium bicarbonate solution and ethyl acetate were added to the reaction mixture and the layers were separated. The product was extracted twice more with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate solution, brine, and then dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the crude product was purified using silica gel column chromatography with a gradient of hexanes / ethyl acetate (l:l-M:2-»l:4-»0:100) followed by ethyl acetate / methanol (50:1) to afford compound 53.1 (287 mg, 0.846 mmol, 54%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde.

Reference:
Patent; SUNESIS PHARMACEUTICALS, INC.; WO2006/65703; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 14160-93-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 14160-93-1, name is 4-Amino-6-chloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of piperazine-1-carboxylic acid (4-isopropoxy-phenyl)-amide (302.1 mg, 1.15 mmol) and 4-amino-6-chloro-pyrimidine-5-carbaldehyde (157 mg, 1.0 mmol) in DMSO (2 mL) was added DIEA (258.5 mg, 2.0 mmol). The mixture was kept stirring at 100 C. for 2 h and MeONH2.HCl (167 mg, 2.0 mmol) was added. The resulting mixture was heated at 100 C. for 0.5 h. It was diluted with water and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude oil was subjected to flash column chromatography on silica gel (EtOAc as eluent) to yield the title compound (45 mg, 11%). 1H NMR (CDCl3) delta 8.19 (s, 1H), 8.12 (s, 1H), 7.21 (d, J=8.93 Hz, 2H), 6.81 (d, J=8.94 Hz, 2H), 6.45 (br, 1H), 4.46 (m, 1H), 3.96 (s, 3H), 3.58 (m, 4H), 3.42 (m, 4H), 1.30 (d, J=6.06 Hz, 6H); LC/MS (ESI) calcd for C20H28N7O3 (MH)+ 414.2, found 414.4.

According to the analysis of related databases, 14160-93-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; US2006/281755; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 14160-93-1, name is 4-Amino-6-chloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. name: 4-Amino-6-chloropyrimidine-5-carbaldehyde

6-Chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine (28) [0170] A suspension of (methoxymethyl)triphenylphosphonium chloride (276.0 g, 0.807 mol, 1.1 equiv) in THF (1.5 L) was cooled in an ice/salt bath to -2 C. and 1 M potassium tert-butoxide (KOtBu) in THF (807 mL, 0.807 mol, 1.1 equiv) was added over 1.5 h at -2 to -3 C. The deep red-orange mixture was stirred at -2 to -3 C. for 1 h. 4-Amino-6-chloropyrimidine-5-carbaldehyde (115.2 g, 0.7338 mol, 1.0 equiv) was then added portion wise to the reaction mixture as a solid form using THF (200 mL) to rinse the container and funnel. During the addition the reaction temperature increased from -3 to 13 C. and a brown color developed. When the reaction temperature dropped to 10 C., the cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature and stirred at ambient temperature for 42 h. The reaction mixture was cooled to -2 C. before being quenched by the slow addition of saturated NH4Cl aqueous solution (750 mL). The mixture was concentrated under reduced pressure to remove most of the THF. The residue was partitioned between EtOAc (3 L) and H2O (1 L). The organic phase was filtered to remove insoluble material at the interface, then extracted with 2 N HCl (4×250 mL) followed by 3 N HCl (2×250 mL). The combined HCl extracts were back-extracted with EtOAc (500 mL) then filtered through Celite to remove insoluble material. The filtrate was cooled in an ice/brine bath, adjusted to pH 8 with a 6 N aqueous NaOH solution and extracted with EtOAc (3×1 L). The combined EtOAc extracts were washed with brine (1 L), dried over Na2SO4, stirred with charcoal (10 g) and silica gel (10 g) for 1 h. The mixture was filtered through Celite, washing the Celite pad with EtOAc (1 L). The filtrate was concentrated, co-evaporating residual EtOAc with n-heptane (500 mL). The resulting tan solid was pumped under high vacuum for 2 h to afford crude 6-chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine (72.3 g, 136.2 g theoretical, 53.1%). The crude desired product was used in the following reaction without further purification. A sample of crude product (2.3 g) was purified by silica gel column chromatography on, eluting with 0-35% EtOAc/n-heptane to give 1.7 g of pure 6-chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine as a white solid, which was found to be a 1 to 2 mixture of E/Z isomers. 1H NMR (300 MHz, DMSO-d6) for E-isomer: delta 8.02 (s, 1H), 7.08 (bs, 2H), 6.92 (d, 1H, J=13.1), 5.35 (d, 1H, J=13.0 Hz), 3.68 (s, 3H) ppm and for Z-isomer: delta 8.06 (s, 1H), 7.08 (bs, 2H), 6.37 (d, 1H, J=6.8 Hz), 5.02 (d, 1H, J=6.7 Hz), 3.69 (s, 3H) ppm; C7H8ClN3O (MW, 185.61), LCMS (EI) m/e 186/188 (M++H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde.

Reference:
Patent; Incyte Corporation; Liu, Pingli; Wang, Dengjin; Wu, Yongzhong; Cao, Ganfeng; Xia, Michael; US2014/256941; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 14160-93-1 ,Some common heterocyclic compound, 14160-93-1, molecular formula is C5H4ClN3O, 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 solution of 4-amino-6-chloropyrimidine-5-carbaldehyde (F1) (7.62 mmol, 1.2 g) was dissolved in a mixture of 25 ml of glacial acetic acid and 4 ml of water,Methoxyamine hydrochloride (13.71 mmol, 1.14 g) was added,The reaction was carried out at 25 C overnight.After completion of the reaction, 20 ml of water was added to the reaction mixture, and the mixture was extracted with 50 ml of ethyl acetate. The organic layer was washed with water 3 times, 10% sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, The solvent was distilled off and purified by column chromatography (eluent petroleum ether: ethyl acetate = 3: 1) to give a white solid in 99% yield.

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. 14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shan Dong University; Zhao, Guisen; Lu, Jinjie; Wang, Guanjie; Yang, Dezhi; Zhang, Zhen; Jing, Yongkui; (32 pag.)CN106045918; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 14160-93-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 14160-93-1, name is 4-Amino-6-chloropyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

To a mixture of trimethoxybenzylamine (469 mg, 2.38 mmol, 1.0 equiv., HCl salt free based prior to use), 4 angstrom molecular sieves (290 mg), and aldehyde 15.2 (375 mg, 2.38 mmol, 1.0 equiv.) in dichloromethane (5 mL) was added acetic acid (0.14 mL, 2.43 mmol, 1.02 equiv.). After stirring for 3 hr at RT, sodium triacetoxyborohydride (757 mg, 3.57 mmol, 1.5 equiv.) was added and the reaction mixture was stirred at RT for 21.5 hr. The reaction mixture was diluted with dichloromethane (20 mL) and aqueous saturated NaHCO3 (20 mL). The aqueous layer was extracted with dichloromethane (4¡Á20 mL), and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resultant crude residue and Boc2O (524 mg, 2.38 mmol, 1 equiv.) were dissolved in THF (10 mL), and pyridine (0.59 mL, 5.95 mmol, 2.5 equiv.) was added. After stirring at RT for 16.5 hr, the reaction mixture was diluted with water (25 mL), EtOAc (25 mL), and 1 N aqueous HCl (25 mL). The aqueous layer was extracted with EtOAc (4¡Á30 mL). The combined organic extracts were washed with water (50 mL), 1 N aqueous HCl (50 mL), and brine (50 mL), dried over anhydrous sodium sulfate, and concentrated. Purification by flash column chromatography (50-60-66% EtOAc/hexanes) afforded compound 15.3 (403 mg, 39% over 2 steps) as a beige foam. LCMS: m/z: 439 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 14160-93-1, blongs to pyrimidines compound. Computed Properties of C5H4ClN3O

4-benzyloxy-3-chloro-phenylamine Compound 1c (8.9 g, 38 mmol) was added to a solution of Compound 1b (6.0 g, 38 mmol) and Et3N (10.6 mL, 76 mmol) in DMSO (38 mL, 1M). The mixture was warmed at 100 C. for 3 hrs. The reaction mixture was cooled, then diluted with H2O and extracted with EtOAc (3¡Á). The organic extract was washed with H2O (4¡Á), concentrated onto SiO2 (30 g) and purified via column chromatography (Horizon, 65+, 60 to 100% EtOAc/hexanes) to afford 4-amino-6-(4-benzyloxy-3-chloro-phenylamino)-pyrimidine-5-carbaldehyde Compound 14 (8.29 g, 61%) as a yellow solid. H E NMR (400 Mhz, CD3OD, warm) delta 10.15 (s, 1H), 8.05 (s, 1H), 7.77 (d, J=2.4 Hz, 1H), 7.48 (d, J=76 Hz, 2H), 7.38 (m, 4H), 7.11 (d, J=8.8 Hz, 1H), 5.18, (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,14160-93-1, its application will become more common.

Reference:
Patent; Connolly, Peter J.; Hughes, Terry V.; Wetter, Steven K.; US2009/111810; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia