Category: pyrimidines

Application of 34253-03-7, 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 34253-03-7 as follows.

Synthesis of pyrimidin-2-ylmethanol:To a stirred solution of methyl pyrimidine-2-carboxylate (10.0 g, 72.46 mmol) in EtOH (100 mL) was added NaBH4 (3.85 g, 101.31 mmol) portion wise at 0 C under inert atmosphere. The reaction mixture was warmed to RT and stirred for 2 h. After completion of starting material by TLC, the volatiles were evaporated under reduced pressure. The residue was diluted with saturated K2C03 solution and extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to afford pyrimidin-2-ylmethanol (4.5 g, crude) as yellow semisolid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.76 (d, 2H), 7.42 (t, 1H), 5.29 (br s, 1H), 4.61 (s, 2H); LC-MS: 94.12%; 111 (M++l) (column; Chromolith RP-18, (100×4.6 mm); RT 2.24 min. 5mM NH4OAc: ACN; 0.8 ml/min); TLC: 100% EtOAc (Rf: 0.2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,34253-03-7, its application will become more common.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1235451-38-3, 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 1235451-38-3 as follows.

To a mixture of compound S1 (1 equiv), AcOK (3 equiv), and compound 2 (1.2 equiv) in dioxane (10 vol) stirred at room temperature under nitrogen was added Pd(dppf)Cl2(0.05 equiv) in one portion. The resulting mixture was stirred at 90 C. under nitrogen for 3 h. After cooling the reaction mixture to room temperature and directly used in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1235451-38-3, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 17180-94-8, name is 5-Chloropyrimidine, molecular formula is C4H3ClN2, 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. HPLC of Formula: C4H3ClN2

Take 25mL reaction flask, add 5-chloropyrimidine (22.8mg, 2.0mmol),P-methoxyphenol (37.2 mg, 3.0 mmol),CuI (19.0 mg, 0.05 mmol),N-5-methoxy-1,1-biphenyl-N’-benzylaldehyde oxalate (18.0 mg 0.05 mmol)K3PO4 (466.0 mg, 2.2 mmol),The reaction flask was then evacuated and backfilled with argon three times, adding 5.0 mL of dimethylsulfoxide Sulfone as a solvent. The reaction mixture was stirred at 120 C for 30 hours. Upon completion of the reaction, after cooling to room temperature, the crude product was added to ethyl acetate and transferred to a separatory funnel, brine was added, and the organic phase was extracted and combined. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was separated through a plug of silica gel to give the corresponding 5- (4-methoxyphenyl) pyrimidine as a yellow oil (28.3 mg, 70%).

With the rapid development of chemical substances, we look forward to future research findings about 17180-94-8.

Reference:
Patent; Funing Xunpeng New Materials Technology Co., Ltd.; Cao Shuguang; (8 pag.)CN106496109; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 53557-69-0 ,Some common heterocyclic compound, 53557-69-0, molecular formula is C4H4IN3, 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 16: tert-Butyl 4-(6-aminopyrimidin-4-yI)-2-(5-chloro-2-methylphenyl)-1 H-pyrrole-1 -carboxylate (XXI) The crude tert-butyl 2-(5-chloro-2-methylphenyl)-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrole-1 -carboxylate (392 mg, 0.94 mmol), Na2003 (250 mg, 2.36 mmol), PdC2(dppf) (77 mg, 0.094 mmol) and 6-iodopyrimidin-4-amine (311 mg, 1.41 mmol) were degassed and purged with argon and suspended in degassed 1,4-dioxane (3 mL) and water (1 mL). The reaction mixture was heated to 110 00 (oil bath temperature) for 2 h. Thesolution was diluted with EtOAc and washed with water. After drying over anhydrous Na2SO4, the organic layer was evaporated. The crude was purified by chromatography on silica gel (hexane/EtOAc 8:2) providing the title compound (220 mg, 58%).1H NMR (600 MHz, DMSQ-d6) 8.55 (s, 1 H), 7.79 (s, 1H), 7.41 (d, 1H), 7.29 (d, 1H), 7.16 (m, 1H), 6.98 (s, 1H),6.66 (s, 1H), 2.30 (s, 3H), 1.44 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53557-69-0, its application will become more common.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria Gabriella; BINDI, Simona; CALDARELLI, Marina; NESI, Marcella; ORRENIUS, Sten Christian; PANZERI, Achille; WO2014/19908; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 313339-35-4, 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.313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, molecular weight is 239.08, as common compound, the synthetic route is as follows.

(3) A mixture of 4,6-dichloro-5-carboxy-2-methylthiopyrimidine (prepared in Example 320(1)) 5.00 g, N,N-dimethylacetamide 50 ml, tetrahydrofuran 20 ml and sodium hydride (60%) 1.673 g is stirred for 20 minutes on an ice bath. Methanol 5 ml is dropped thereto over a period of 30 minutes and the mixture is stirred for 15 minutes. The reaction mixture is diluted with a 10% aqueous citric solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo. The resulting solid is triturated with hexane in ice to give 4-chloro-5-carboxy-6-methoxy-2-methylthiopyrimidine as a slightly brown crystalline powder, 4.61 g. mp 179-181 C.

The chemical industry reduces the impact on the environment during synthesis 313339-35-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamada, Koichiro; Matsuki, Kenji; Omori, Kenji; Kikkawa, Kohei; US2004/142930; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 38275-42-2, 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 38275-42-2, name is 5-Chloro-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

n-Butyllithium (5.4 mL, 1.6 M in hexanes, 8.63 mmol) was added dropwise to a solution of 2-(2-(4-fluorobenzyl)thiophen-3-yl)ethanol (0.97 g, 4.11 mmol) in anhydrous tetrahydrofuran (15 mL) at -78 C. The resulting mixture was stirred at -78 C for 1 h and then a solution of 5-chloro-2-(methylthio)pyrimidine (0.79 g, 4.93 mmol) in 1 mL of tetrahydrofuran was added slowly. The mixture was stirred at -78 C for 1 h and then at -40 C for 2 h. The reaction was quenched with a solution (1.1 mL) of acetic acid and methanol (1:1) at -40 C and then a solution of 2,3-dichloro-5,6-dicyano-l,4- benzoquinone (0.1.1 g, 4.93 mmol) in tetrahydrofuran (1 mL) was added. After complete addition the reaction was stirred at -40 0C for 1 h, then warmed to rt. 10 mL of aqueous sodium hydroxide (2 M) and 50 mL of water were added and the mixture was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (80 mL), dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo and the product purified by flash chromatography eluting with ethyl acetate / hexane (1 :4) to afford the title compound (0.45 g, 28%). MS (M+H)+ 395/397.

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 38275-42-2, 5-Chloro-2-(methylthio)pyrimidine.

Reference:
Patent; AMGEN, INC.; WO2006/66172; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 77994-12-8, 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 77994-12-8, name is 2,5-Diaminopyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows.

The water separator is arranged in the reaction vessel by adding the mass fraction of in 75percent cyclohexane 130 ml, phenyltheophylline methanol (3) 0.62mol, solid sodium sulfite 0.13mol, control the stirring speed 180rpm, raising the temperature of the solution 65 °C, heating 4h, the temperature of the solution is then reduced to 45 °C, by adding 2,5-diamino-pyrimidin-4-one (2) 0.73mol, continue to reflux reaction 6h, added after cooling the mass fraction of 15percent sodium chloride solution 300 ml, separating an aqueous layer, the organic layer used for quality score 65percent acetonitrile extraction, merged layer, 68kPa low-pressure distillation until the solution is clarified, reducing the temperature of the solution to 20 °C, by adding the mass fraction is 28percent oxalic acid solution is adjusted to pH 2, separating solid, filtering, in the mass fraction is 95percent nitromethane recrystallizing, to obtain crystal 2-benzyloxy-5-amino-pyrimidin-4-one 124.12g, yield 91percent.

According to the analysis of related databases, 77994-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Science and Technology Co., Ltd. Chester; Peng, Fei; (5 pag.)CN105503740; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4763-35-3 ,Some common heterocyclic compound, 4763-35-3, molecular formula is C5H7N3O2, 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.

Preparation of 89 10240] Step 3. Into a 100 mE round bottom flask equippedwith a magnetic stir bar was placed 2-Amino-4-hydroxy-S-methoxy-pyrimidine (500 mg, 3.54 mmol), anhydrous DMF (30 mE), AA-13 (1.27 g, 5.31 mmol), DI3U (2.12 mE, 14.17 mmol), and HOP (1.96 g, 4.43 mmol). The reaction mixture was allowed to stir at room temperature for 30 minutes then at 50 c. for 16 hours. The solvent was removed under reduced pressure and the residue was partitioned between brine and ethyl acetate. The organic layers were combined, dried (magnesium sulfate), the solids were removed via filtration, andthe solvents of the filtrate were removed under reduced pressure. The crude was purified via reverse phase liquid chromatography (RP Vydac Denali c18-10 jim, 250 g, Scm. Mobilephase 0.25% NH4HcO3 solution in water, methanol), the bestfractions were pooled, the solvents were removed underreduced pressure to afford 89.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4763-35-3, its application will become more common.

Reference:
Patent; McGowan, David; Raboisson, Pierr Jeane-Marie Bernar; Embrechts, Werner; Jonckers, Tim Hugo Maria; Last, Stefaan Julien; Pieters, Serge Maria Aloysius; Vlach, Jaromir; US2014/45849; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 19858-50-5, 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 19858-50-5, name is (2-(Methylthio)pyrimidin-5-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 113 (1.02 g, 653 mrnoi) and PPh3 (3.4g, 131 mmol)in DCM (50 mL) is added carbon tetrabromide (4.3 g, 13.1 rnrnoi). After stirring at room temperature for 16 hours, the mixture is diluted with DCM, washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (EA:PE 1:20) to give 137 as a pale yellow oil (900 mg, 63percent). (MS: [M÷H] 2190)

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 19858-50-5, (2-(Methylthio)pyrimidin-5-yl)methanol.

Reference:
Patent; IMMUNE SENSOR, LLC; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHONG, Boyu; SUN, Lijun; SHI, Heping; LI, Jing; CHEN, Chuo; CHEN, Zhijian; (270 pag.)WO2017/176812; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 51953-18-5, 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 51953-18-5, name is Pyrimidin-4-ol. This compound has unique chemical properties. The synthetic route is as follows.

Method N Preparation of 5-Iodo-4(3H)-pyrimidinone The procedure of Sakamoto et. al. (Chem. Pharm. Bull. 1986, 34(7), 2719- 2724) was used to convert 4(3H)-pyrimidinone into 5-iodo-4(3H)-pyrimidinone, which was of sufficient purity for conversion to 4-chloro-5-iodopyrimidine.

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 51953-18-5, Pyrimidin-4-ol.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/97162; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia