Pyrimidines

Synthetic Route of 161489-05-0, Adding some certain compound to certain chemical reactions, such as: 161489-05-0, name is 4-Iodo-6-methoxypyrimidine,molecular formula is C5H5IN2O, 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 161489-05-0.

General procedure: To a solution of(S)-4-(difluoromethyl)-N-(6-(3,4-dimethylpiperazin-1- yl)-2,4-difluoro-3 -(1,2,3 ,6-tetrahydropyridin-4-yl)phenyl)-6-oxo- 1 ,6-dihydropyridine- 3-carboxamide (31.5 mg, 0.064 mmol, preparation described in Example 34) and 2- bromo-5-methoxypyrimidine (16.89 mg, 0.089 mmol) in 2-propanol (2.5 mL) at RT was added N,N-diisopropylethylamine (0.022 ml, 0.128 mmol). After heating in a microwave reactor at 170 C for 2 h, the reaction mixture was purified on preparatory column eluting with water (containing 0.1% HCOOH)/acetonitrile (containing 0.1% HCOOH) gradient (85/55). The title compound was isolated as an yellow powder (20 mg, 50%). LCMS [M+1j 602.5.

According to the analysis of related databases, 161489-05-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROPELLON THERAPEUTICS INC.; AL-AWAR, Rima; ISAAC, Methvin; JOSEPH, Babu; LIU, Yong; MAMAI, Ahmed; PODA, Gennady; SUBRAMANIAN, Pandiaraju; UEHLING, David; WILSON, Brian; ZEPEDA-VELAZQUEZ, Carlos Armando; (311 pag.)WO2019/46944; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 4774-34-9, name is 4-Hydroxypyrimidine-5-carbonitrile, the common compound, a new synthetic route is introduced below. category: pyrimidines

EXAMPLE 76 4-(1,2,4,5-Tetrahydro-benzo[d]azepin-3-yl)-pyrimidine-5-carbonitrile In analogy to the procedure described in example 4 the 4-chloro-pyrimidine-5-carbonitrile (prepared from 4-hydroxy-5-pyrimidine-carbonitrile and phosphorus oxychloride, phosphorus pentachloride and N-ethyl-N,N-diisopropylamine in acetonitril at reflux) was treated with 2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride [J. Heterocycl. Chem. (1971), 8(5), 779-83] in N,N-dimethylformamide in the presence of N-ethyl-N,N-diisopropylamine at room temperature to yield the 4-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-pyrimidine-5-carbonitrile as off white solid; MS: [M+H]+=251; m.p. 148-150 C.

The synthetic route of 4774-34-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US6218385; (2001); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 101257-82-3, 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. 101257-82-3, name is 4-Amino-5-chloropyrimidine, molecular formula is C4H4ClN3, 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.

L. [4-(3-Chloropropylsulfanyl)-3-methylpyridin-2-ylmethyl]-(5-chloropyrimidin-4-yl)amine A solution of 2.7 g (20.85 mmol) of 4-amino-5-chloropyrimidine in 20 ml of dimethylformamide is added dropwise to a suspension of 0.75 g (18.25 mmol) of sodium hydride (60% strength in paraffin) in 5 ml of dimethylformamide. The mixture is stirred at room temperature for 20 minutes. A solution of 5 g (17.38 mmol) of 2-chloromethyl-4-(3-chloropropylsulfanyl)-3-methylpyridine in 5 ml of dimethylformamide is then added dropwise in the course of 30 minutes and the mixture is then stirred at room temperature for 4 hours. It is concentrated in a high vacuum and the residue is taken up in 150 ml of water and 100 ml of dichloromethane with vigorous stirring. The aqueous phase is extracted with 3*50 ml of dichloromethane. The organic extracts are dried over magnesium sulfate and concentrated. The residue is purified by chromatography on silica gel (eluent: toluene/ethyl acetate/methanol/conc. ammonia=6/3.5/0.5/0.05). The elude is concentrated and the residue is then digested with diethyl ether. After filtration and drying of the precipitate, 2.8 g (47%) of the title compound are obtained as a colorless solid, which is used without further purification.

According to the analysis of related databases, 101257-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BYK Gulden Lomberg Chemische Fabrik GmbH; US6395732; (2002); B1;,
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. 32779-36-5, name is 5-Bromo-2-chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 32779-36-5

Synthesis -Aminomethyl-5-bromopyrimidine[0083] Methylamine (2.0 M in methanol, 40 mL, 80 mmol) was added to 5-bromo-2- chloropyrimidine (5.6 g, 29.0 mmol) in a sealable reaction vessel. After allowing to vent for a few minutes, the vessel was sealed, placed behind a safety shield and heated in a 115 ¡ãC oil bath for 48 hours. Upon cooling the volatiles were removed in vacuo. The material was dissolved in CH2C12 (200 mL) and washed with 1M NaOH (40 mL). The aqueous layer was extracted further with CH2C12 (2×50 mL). The combined organics were dried over MgSC>4, filtered and concentrated yielding an off white solid (5.1 g, 93percent). LCMS (m/z):188.0/190.0 (MH ).

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, 32779-36-5, 5-Bromo-2-chloropyrimidine.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2434-56-2, 4,6-Diaminopyrimidine, 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, 2434-56-2, blongs to pyrimidines compound. Product Details of 2434-56-2

To a suspension of pyrimidine-4, 6-diamine (342.0 mg, 3.10 mmol) and NaHCCb (286.0 mg, 3.40 mmol) in EtOH (20 mL) was added a solution of 2-chloropropanal (0.57 M, 57 mmol) in a mixed solvent of chloroform and hexane (1/2 (v/v), 100 mL). The reaction mixture was stirred in a sealed tube at 85 C overnight, then cooled down to rt and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/20) to give the title compound as brown oil (80.0 mg, yield 17.4%).MS (ESI, pos. ion) m/z: 149.2 [M+H]+;1H NMR (400MHz, DMSO-^) d (ppm): 8.84 (s, 1H), 7.09 (s, 1H), 6.46 (s, 2H), 6.26 (s, 1H), 2.40 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2434-56-2, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 39876-88-5, 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. 39876-88-5, name is 4-Chlorobenzofuro[3,2-d]pyrimidine, molecular formula is C10H5ClN2O, 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.

Finally, 3- [6- (9,9-dimethyl-fluoren-2-yl) dibenzothiophene-4-yl] phenyl boronic acid pinacol ester 0.45g, 4- chlorobenzoate furo [3,2-d ] pyrimidine 0.14g, flask, 0.45g potassium phosphate, dioxane, 4mL, 0.16g t- butanol, a three-necked, flask was replaced air by nitrogen;Then, 1.8mg of palladium acetate, di (1-adamantyl) -n- butyl phosphine was added to 5.6mg pin, and the mixture was allowed to promote the reaction to reflux.Water was added to the obtained mixture, and the solution was extracted with ethyl acetate.Washed with saturated aqueous sodium chloride, the addition of magnesium sulfate, and filtered nature.Removing the solvent of the filtrate was evaporated, toluene: hexane = 1: 5 by purifying the (volume ratio) by flash column chromatography using as a developing solvent to obtain a yellow solid in a yield of 10%.It shows a synthetic scheme of Step 5 in the formula (e-3).

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 39876-88-5, 4-Chlorobenzofuro[3,2-d]pyrimidine.

Reference:
Patent; Handotai Enerugi Ken kyushu Corporation; Inoue, Hideko; Ghanamoto, Miki; Seo, Hiromi; Takahashi, Tsuyoshi; Nakagawa, Tomoka; (80 pag.)KR2015/132837; (2015); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 165807-05-6 , The common heterocyclic compound, 165807-05-6, name is 4-Dimethoxymethylpyrimidin-2-ylamine, molecular formula is C7H11N3O2, 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.

General procedure: Reactions were performed with 0.30 mmol of4-(dimethoxymethyl)pyrimidin-2-amine (1a), 0.30 mmol of aldehyde 2, 0.30 mmol of malonate 3 in 3.0mL of p-xylene in the presence of 20 molpercent catalyst A1 or A5 at 50 ¡ãC and stirred for 48?60 h. Aftercompletion of the reaction (as observed by TLC), the crude product was purified by preparative TLC(GF254 silica gel: hexane/EtOAc = 5/1), which yielded the target product

The synthetic route of 165807-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bai, Song; Liu, Shan; Zhu, Yunying; Wei, Xian; Zhao, Kunhong; Li, Weihua; Wu, Qin; Heterocycles; vol. 96; 8; (2018); p. 1383 – 1397;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 38275-55-7, 5-Fluoropyrimidine-2-carbonitrile, 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, Formula: C5H2FN3, blongs to pyrimidines compound. Formula: C5H2FN3

Method 50; 5-Fluoropyrimidine-2-carbaldehvde; To a solution of 5-fluoropyrimidine-2-carbonitrile (Method 6, 1.0 g, 8.1 mmol) in anhydrous TetaF at -780C was added a solution of DIBAL-eta (8.1 mL) over a period of 20 minutes. The resulting mixture was stirred at this temperature for 2hours whereupon MeOH was added. The solution was allowed to warm to room temperature whereupon a solution of cone. HCl was added. The resulting mixture was stirred for 2 hours at ambient temperature and the aqueous layer was washed with EtOAc (3x). The combined organic extracts were washed with brine and dried (MgSO4). Evaporation of the solvent afforded the titled compound (780 mg, 76%). MS: [M+eta]+ 127.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38275-55-7, 5-Fluoropyrimidine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/49041; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 287714-35-6 , The common heterocyclic compound, 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, 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.

Step 3b. 2-[2-Chloro-5-(2-chloro-4-methanesulfonyl-benzoylamino)-phenyl]-pyrimidine-5-carboxylic acid methyl ester (compound 1002-7) A mixture of 1001-7 (200 mg, 1.1 mmol), 1-9 (756 mg, 1.6 mmol) and Pd(PPh3)4(60 mg, 0.05 mmol) in saturated NaHCO3 (2 mL) and DMSO (6 mL) was stirred at 100 C. for 3 h. After cooling to room temperature, NaOH (43 mg, 1.1 mmol) was added to reaction solution and stirred for 0.5 h. The reaction mixture was extracted with ethyl acetate. The aqueous layer was adjusted pH to 6 with 1.2 M HCl and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, concentrated to afford crude acid (300 mg) without further purification. The mixture of the crude acid (300 mg) in MeOH (15 mL) and H2SO4 (0.25 mL) was stirred at 85 C. for 1 h. After removal of solvent, the residue was partitioned between water and ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4. The crude product was purified by column chromatography (hexanes/ethyl acetate: 1/1) to afford compound 1002-7 as a white solid (160 mg, 78% yield via two steps). LCMS: m/z 480.2 [M+1]+. 1H NMR: (400 MHz, CDCl3): delta 3.36 (s, 3H), 3.96 (s, 3H), 7.65 (d, J=8.8 Hz, 1H), 7.81 (dd, J=8.8 Hz, J=2.4 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H), 8.02 (dd, J=8.0 Hz, 1.6 Hz, 1H), 8.14 (d, J=1.2 Hz, 1H), 8.30 (d, J=2.4 Hz, 1H), 9.40 (s, 2H), 11.02 (s, 1H).

The synthetic route of 287714-35-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genetech, Inc.; Curis, Inc.; Cai, Xiong; Qian, Changgeng; Zhai, Haixiao; US2014/18368; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 65996-50-1, 1H-Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione, 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, Computed Properties of C6H5N3O2, blongs to pyrimidines compound. Computed Properties of C6H5N3O2

A suspension of lH-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (0.38 g, 2.52 mmol) in phosphorus oxychloride (30 mL) was heated to 120 for 6 h during which the mixture became clear and homogeneous. The mixture was allowed to cool to room temperature and the excess phosphorus oxychloride was removed in vacuo. The residue was cooled in ice, cold ammonium hydroxide (30 mL, pH=8) was added and the mixture stirred for 30 min. The precipitate was collected and washed with cold water. The solid was dried in vacuo to afford 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (0.33 g, 70%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65996-50-1, 1H-Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2009/62258; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia