Pyrimidines

Application of 871254-61-4, Adding some certain compound to certain chemical reactions, such as: 871254-61-4, name is 2,4-Dichloropyrimidine-5-carbaldehyde,molecular formula is C5H2Cl2N2O, 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 871254-61-4.

Example 18 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine To a stirred solution of hydrazine (Aldrich, 64 mg, 2 mmol) in THF (5 mL), 2,4-Dichloro-pyrimidine-5-carbaldehyde (Example 17, 176 mg, 1 mmol) was added and the mixture was stirred at room temperature for 30 min. The mixture was poured into water and extracted with EtOAc. The extract was dried with sodium sulfate and the solvent was removed to give an orange solid. 128 mg, 82%. MS (M+H)+, 155.

According to the analysis of related databases, 871254-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Roberts, John Lawson; US2005/277655; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22536-61-4, 2-Chloro-5-methylpyrimidine, 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, Application In Synthesis of 2-Chloro-5-methylpyrimidine, blongs to pyrimidines compound. Application In Synthesis of 2-Chloro-5-methylpyrimidine

A 3 L 3 -neck round bottomed flask was fitted with a reflux condenser, a temperature controller and a septum and charged with 2-chloro-5-methylpyrimidine (81 mL, 778 mmol), potassium vinyltrifluoroborate (156 g, 1167 mmol), triphenylphosphine (18.02 mL, 78 mmol), cesium carbonate (156 mL, 1945 mmol) and a large stir bar. Water (1565 mL) was added, and the mixture was stirred for several min before THF (244 mL) was added. Argon was bubbled through the mixture for 5 min and then palladium (II) chloride (1.72 g, 38.9 mmol) was added. The reaction was further sparged with argon for 5 mins. The temperature was raised to 62 C and stirring was continued to completion. The reaction was then cooled to RT and filtered through two Whatman GF/F filter cups, rinsing with ether. The mixture was transferred to a separatory funnel, and the layers were separated. The aqueous layer was further extracted with diethyl ether (4 x 200 mL). The organic layers were combined and dried over anhydrous MgS04 and then filtered. The mixture was partially concentrated on the rotary evaporator at 20 C and 115 torr for an extended period of time to give an orange liquid. The material was further purified by Kugelrohr distillation to isolate the title compound (65.4g, 70%) as a light yellow oil. NMR (400 MHz, CDC13) delta 2.31 (s, 3H), 5.68 (d, J=10.56 Hz, 1H), 6.55 (d, J=17.22 Hz, 1H), 6.86 (dd, J=17.41, 10.56 Hz, 1H), 8.54 (s, 2H). LCMS-ESI (pos.) m/z: 121.1 (M+H)+.

The synthetic route of 22536-61-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; SHARMA, Ankit; (321 pag.)WO2018/93576; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 6554-61-6 , The common heterocyclic compound, 6554-61-6, name is 4,5-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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.

1- { 3- [2-methoxy-5 -nitro-4-(tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenoxy]propyl }pynolidine (500 mg, 1.23 mmol), 4,5-dichloropyrimidine (220 mg, 1.48 mmol), Pd(amphos)C12 (59 mg, 0.08 mmol) and 2M sodium carbonate (1.23 mL, 2.46 mmol) were combined in 1,4-dioxane (5 mL). The mixture was purged with N2 for 6 mm, sealed and left stifling at 90 C for 45 minutes. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combinedorganic layers were washed with water. After removal of the organic solvents under reduced pressure, the residue was purified by flash chromatography on silica gel column eluted with 0-100% solvent A in CH2C12 (solvent A: 0.2% NH4OH/10% MeOH/88.9%CH2C12) to provide the title compound as a brown solid (422 mg, 87%). MS (ESI, pos. ion) mlz: 393.0 (M+1).

The synthetic route of 6554-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; YU, Chul; YU, Ming; ZANCANELLA, Manuel; LI, Zhe; (202 pag.)WO2018/226998; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.Quality Control of 2-Chloro-5-ethylpyrimidine

[0761] A mixture of (S)-3-((4-bromophenoxy)methyl)pyrrolidine hydrochloride (1.15 g, 3.9 mmol), 2- chloro-5-ethylpyrimidine (0.62 g, 4.3 mmol) and diisopropylethylamine (1.27 g, 9.7 mmol) in dimethylformamide (50 mL) was stirred at 130oC overnight. After cooling to ambient temperature, dimethylformamide was removed under reduced pressure and the residue was treated with water (200 mL). A brown precipitate was formed and then the mother liquor was decanted. The precipitate was re- dissolved in dichloromethane, dried over sodium sulfate and purified on a 3 cm silica gel pad eluted with hexanes: ethyl acetate mixture gradient (4:1 to 2:1) to afford the title product (0.73 g, 51 %) as colorless powder.1H-NMR (400 MHz, DMSO-d6) delta 8.21 (s, 2H), 7.44 (d, J = 9.0 Hz, 2H), 6.94 (d, J = 9.0 Hz, 2H), 4.12- 3.87 (m, 2H), 3.75- 3.55 (m, 2H), 3.52- 3.39 (m, 1H), 3.37- 3.26 (m, 1H), 2.79 – 2.64 (m, 1H), 2.41 (q, J = 7.5 Hz, 2H), 2.20- 2.05 (m, 1H), 1.91- 1.75 (m, 1H), 1.11 (t, J = 7.6 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,111196-81-7, 2-Chloro-5-ethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PRAMANA PHARMACEUTICALS INC.; CHAFEEV, Mikhail; (240 pag.)WO2019/104418; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 31169-25-2, 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 31169-25-2 as follows.

7-bromothieno[3,2-d]pyrimidin-4(3H)-one (5.9 g) was dissolved in POCl3 (20 mL) and the reaction mixture was stirred at 150 C. for 3 hours. The reaction mixture was cooled to room temperature, and remaining POCl3 was concentrated and placed in ice water. The solid thus obtained was washed with sodium bicarbonate and dried using nitrogen gas. The resulting compound was further dried over anhydrous sodium sulfate, and filtered and distilled under reduced pressure to obtain the title compound (1.0 g, 39%). [0175] 1H NMR (300 MHz, DMSO-d6): delta 9.16 (s, 1H), 8.79 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31169-25-2, its application will become more common.

Reference:
Patent; HANMI PHARM. CO., LTD; Son, Jung Beom; Kim, Nam Du; Chang, Young Kil; Kim, Hee Cheol; Kim, Ji Sook; Jung, Young Hee; US2013/274268; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6554-61-6, 4,5-Dichloropyrimidine, 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, Safety of 4,5-Dichloropyrimidine, blongs to pyrimidines compound. Safety of 4,5-Dichloropyrimidine

A solution of 4,5-dichloropyrimidine (0.15 mL, 1.5 mmol) and 2-((pyridin-2-ylmethyl)thio)-1 /-/- benzo[d]imidazole R (300 mg, 1.24 mmol) in dry DMF (1.5 mL) was treated with a 60% mineral oil dispersion of sodium hydride (55 mg, 1.4 mmol), stirred at RT for 5 min then heated to 70C for 90 min. The mixture was treated with saturated aqueous ammonium chloride solution (2 mL), diluted with EtOAc (40 mL), washed with water (3 x 40 mL) and brine, dried (MgSCU) and chromatographed on a basic silica column eluting with 0-100% EtOAc / PE. The product was purified further by mass-directed prep. HPLC eluting with MeCN-H20 to give 1-(5-chloropyrimidin-4-yl)-2-((pyridin-2-ylmethyl)thio)-1 /-/- benzo[d]imidazole 59 (22 mg, 5%) as a pale orange gum. 1H NMR (500 MHz, CDC) delta 9.15 (s, 1H), 8.96 (s, 1H), 8.52 (d, J = 4.3 Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H), 7.60 (td, J = 7.7, 1.8 Hz, 1H), 7.47 (d, J = 7.8 Hz, 1H), 7.36-7.29 (m, 1H), 7.25- 7.20 (m, 1H), 7.16 (dd, J = 6.8, 5.0 Hz, 1H), 7.05 (d, J = 8.0 Hz, 1H), 4.77 (s, 2H); LCMS (method B): 2.23 min (354.2, MH+).

The synthetic route of 6554-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDAG CROP PROTECTION LTD; URCH, Christopher, John; BUTLIN, Roger, John; CHRISTOU, Stephania; BOOTH, Rebecca, Kathryn; (111 pag.)WO2018/130838; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 862730-04-9, 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.862730-04-9, name is 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C8H10IN5, molecular weight is 303.1, as common compound, the synthetic route is as follows.

Synthesis of 3-(3-bromo-5-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA85); A solution of 2-(3-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (137 mg, 0.43 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (65 mg, 0.216 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA85 (28 mg, 36% yield). ESI-MS (M+H)+ m/z calcd 362.1, found 362.0.

Statistics shows that 862730-04-9 is playing an increasingly important role. we look forward to future research findings about 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C4H4BrN3

General procedure: A mixture of bromo compound (1 .0 eq.) and bis(pinacolato)diboron (1 .1 eq.) and potassium acetate (2.0 eq.) dissolved in 1 ,4-dioxane (10 vol) was degassed with argon gas for 15 mm. Subsequently, PdCI2(dppf)CH2C12 (0.05 eq.) was added and the reaction mixture was stirred at 85-100 CC for 16 h. The reaction mixture (generally black color) was filtered and concentrated under reduced pressure. The resulting black mixture was used further without any purification. Intermediate 1-40 was prepared according to the general boronic ester synthesis procedure A by utilizing 5-bromopyrimidin-2-amine (reaction time: 5 h, temperature: 100C). 1H NMR (400 MHz, DMSO) 68.59(s, 2H), 5.43 (brs, 2H), 1.32 (5, 12H);

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, 7752-82-1, 5-Bromopyrimidin-2-amine.

Reference:
Patent; IRM LLC; NOVARTIS AG; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; PARASELLI, Prasuna; KONDREDDI, Ravinder Reddy; LEONG, Seh Yong; MISHRA, Pranab Kumar; MOREAU, Robert Joseph; ROLAND, Jason Thomas; SIM, Wei Lin Sandra; SIMON, Oliver; TAN, Liying Jocelyn; YEUNG, Bryan KS; ZOU, Bin; BOLLU, Venkatataiah; WO2014/78802; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 58347-49-2, 7-Chloropyrazolo[1,5-a]pyrimidine, 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, 58347-49-2, blongs to pyrimidines compound. Formula: C6H4ClN3

A solution of 7-chloropyrazolo[1,5-ajpyrimidine (0.05 g, 0.326 mmol), (8)-tert-butyl (1 -(2-chloro-4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate (prepared as described in Example 260, Part A and B) (0.152 g, 0.326 mmol), C52CO3 (0.212 g, 0.65 1 mmol), and KBr (0.039 g, 0.326 mmol) in 1,4-dioxane (10 mL) and water (1 mL) was purged with nitrogen gas for 30 mi PdC12 (dppf)-CH2C12 adduct (0.027 g, 0.033 mmol) was added to the reactionmixture and the solution was purged with nitrogen gas again for 10 mm. The reaction mixture was heated at 80 C for 12 h. The reaction mixture was concentrated and the residue obtained was dissolved in ethyl acetate (30 mL) and water (30 mL). The biphasic mixture was filtered through diatomaceous earth. The diatomaceous earth was washed with ethyl acetate (50 mL). The organic layer wasseparated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford cmde product as a brown solid which was purified by silica-gel column chromatography (pet ether/ethyl acetate) to afford (5)-tert-butyl (1 -(2-chloro-4- (pyrazolo [1,5 -aj pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-yl)carbamate (0.08 g, 0.174 mmol, 54% yield) as an off-white solid. LCMS (ESI) m/e 459.2 [(M+H) ,calcd for C24H32C1N403 459.21; LC/MS retention time (Method Al): tR = 3.28 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1193-21-1, 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. 1193-21-1, name is 4,6-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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.

Sodium thiomethoxide (28.2 g, 0.403 mol) was suspended in 350 mL of THF and stirred at ambient temperature under a blanket of nitrogen gas while 4,6- dichloropyrimidine (50 g, 0.33 mol) was added. After the addition was completed, the reaction was stirred and heated at 60 0C for 4 hours. The solvent was removed under reduced pressure and the residue was dissolved into 500 mL of 0.25N sodium hydroxide and extracted 3 times with ethyl acetate. The organics were combined and backwashed with water, brine, and 1: 1 brine/lN HCl. The combined organic layer was dried (Na2SO4 anh.) and the solvent was removed under reduced pressure. The crude material was re- crystallized from hot petroleum ether to afford ~24 g of material. LC/MS (M+l): 161.

According to the analysis of related databases, 1193-21-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/85913; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia