Pyrimidines

Reference of 148550-51-0, 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.148550-51-0, name is Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, molecular formula is C8H10N2O4S, molecular weight is 230.24, as common compound, the synthetic route is as follows.

A solution of (E)-2-chloro-l l-(piperazin-l-yl)dibenzo[b,f][l,4]oxazepine (0.25 g, 0.8 mmol) and ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (0.13 g, 0.57 mmol) in DME was stirred at room temperature for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with saturated aqueous solution of bicarbonate, water, acetic acid and sodium acetate (pH=4), dried over sodium sulfate and solvent evaporated. The resulting crude residue was purified by flash chromatography (0percent to 30percent ethyl acetate in hexane) to afford title compound 116 (0.265 g, quant.).

Statistics shows that 148550-51-0 is playing an increasingly important role. we look forward to future research findings about Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate.

Reference:
Patent; METHYGENE INC.; EN VIVO PHARMACEUTICALS, INC.; WO2008/55068; (2008); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 66131-68-8, 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 66131-68-8, name is 2-Chloro-N-methylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-(5-chloro-2,4-dimethoxyphenyl)-7-(piperazin-1-yl)imidazo[1,2-a]pyridine 301 (200 mg, 0.53 mmol) and N,N-diisopropylethylamine (0.4 mL, 2.29 mmol) in DMF (5 mL) was charged with 2-chloro-N-methylpyrimidin-4-amine ( 155 mg, 1.07 mmol). The reaction mixture was stirred at 100 C for 16 h. The reaction mixture was cooled to room temperature, suspended in water and stirred for 1 h. The precipitate was collected by filtration; the solid obtained was washed with water, dried under reduced pressure and purified by combi-fash companion (silica gel, CH3OH/CH2Cl2). The product was further triturated with methanol and filtered. The solids were washed with hexanes and dried to provide 2-(4-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-a]pyridin-7-yl)piperazin-1-yl)-N-methylpyrimidin-4-amine 418a (20 mg, 8%) as light brown solid. 1H NMR (300 MHz, DMSO-d6) delta 8.34 i d . ./ 7.5 Hz, 1H), 8.15 (s, 1H), 8.04 (s, 1H), 7.75 (br s, 1H), 6.97 (br s, I I I ) . 6.89 (s, IH), 6,87 (s, 1H), 6,71 (s, i l l ). 5.78 (d, ./ 5,7 Hz, 1H), 4.01 (s, 3H), 3.93 (s, 3H), 3.83 (br s, 4H), 3.33 (br s, 4H), 2,78 (d, ,/ 4.2 Hz, 3H): HPLC (Method 1 ) 92.8% (AUC), fR = 1 1.85 min.; ESI+APCI MS m/z 480 [M + Hf.

According to the analysis of related databases, 66131-68-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); 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. 1780-32-1, name is 2,4-Dichloro-5,6-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1780-32-1

To a solution of 2,4-dichloro-5,6-dimethylpyrimidine (0.800 g, 4.55 mmol) in EtOH (40 mL) were added Na2CO3 (2.42 g, 22.8 mmol) and 1H-indazol-5-amine (0.605 g, 4.55 mmol). The resulting mixture was stirred for 12 h at 100 C. The solvent was removed under reduced pressure and the residue was poured into water (50 mL) and extracted with EtOAc (3 x 100 mL). The organic phase was dried over Na2 SO4, filtered and concentrated under reduced pressure to give a residue which was purified by column chromatograph on silica gel (eluted with PEEA = 1:1) to provide the title compound (120 mg, yield: 9.7%) as a white solid.

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, 1780-32-1, 2,4-Dichloro-5,6-dimethylpyrimidine.

Reference:
Patent; KADMON CORPORATION, LLC; KIM, Ji-in; LIU, Kevin; POYUROVSKY, Masha; LU, Dan; ZHU, Zhenping; WO2015/54317; (2015); 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.1215787-31-7, name is 6-Bromo-4-chloropyrido[2,3-d]pyrimidine, molecular formula is C7H3BrClN3, molecular weight is 244.4758, as common compound, the synthetic route is as follows.Formula: C7H3BrClN3

Add 24.2 g (0.1 mol) of 4-chloro-6-bromopyrido[2,3-d]pyrimidine, 7.4 g (0.1 mol) of propylenediamine and 400 ml of 1,4-dioxane to a 1 L round bottom flask. The mixture was heated to 60 C, and the reaction was monitored by TLC until the reaction was completed, and the solvent was evaporated to givethe compound 8-1 18.9 g of white solid (yield: 79.8%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1215787-31-7, 6-Bromo-4-chloropyrido[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Heilongjiang University Of Traditional Chinese Medicine; Chen Hong; Chen Qun; Li Yan; Liu Yan; Song Qiannan; Wang Lin; Su Yuming; Liu Linlin; Dai Jinzhu; Guo Jianbo; Li Fei; Lu Lu; Guo Wei; (18 pag.)CN109836423; (2019); A;,
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. 106157-82-8, name is 1-(2-Aminopyrimidin-4-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 1-(2-Aminopyrimidin-4-yl)ethanone

Step C: Preparation of tert-Butyl [7- {2- [L- (2-AMINO-] [PYRIMIDIN-4-YL)-ETHYLAMINO]-BENZOYLAMINO}-4,] 4-dimethyl-3,4- [DIHYDRO-LH-ISOQUINOLINE-2-CARBOXYLATE] To a solution of [1-(2-AMINO-PYRIMIDIN-4-YL)-ETHANONE] (Step B, 200 mg, 1.46 mmol) in toluene (15 mL) was added, 7- [(2-AMINO-BENZOYLAMINO)-4,] 4-dimethyl-3, [4-DIHYDRO-LH-] isoquinoline-2-carboxylic acid tert-butyl ester (Example 15, Step A) (288 mg, 0.73 mmol), and HOAc (3 drops). The resulting mixture was heated at [95 C] under N2 for 20 h. The reaction was cooled to RT and NaBH (OAc) 3 (620 mg, 2.92 mmol) was added and reheated for 3 h. The reaction was cooled to RT, quenched with [NA2CO3] solution (2 M, 5 mL), solvent was evaporated in vacuo. The residue was extracted with CHC13. The organic layer was washed with saturated [NAHC03,] water, brine, dried over [MGS04,] and evaporated in vacuo. The crude solid was purified by chromatography on silica gel. Elution with [CH2CL2 : MEOH] (95: 5) gave THE final compound. MS [M/Z] : 517.3 (M+H). [CALC’D.] for [C2GH37N603-] 517.63.

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, 106157-82-8, 1-(2-Aminopyrimidin-4-yl)ethanone.

Reference:
Patent; AMGEN INC.; WO2004/5279; (2004); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 6299-25-8, 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 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 4, 6-Dichloro-2-methylsulfanyl-pyrimidine 0103 (5.0 g, 25.6 mmol) in CH2Cl2 (15 mL) at 0 0C was added meta-chloroperoxybenzoic acid (11.06 g, 64.1 mmol) over a period of 20 minutes. The reaction was allowed to warm to room temperature and stirred for 2.5 hours. The mixture was filtrated and the filtrate was concentrated. The resulting residue was washed with saturated Na2CO3 solution and ether to form a white solid which was dried to obtain the title compound 0104 (2.6g, 44%): LCMS: 227 [M+l]+; 1H NMR (CDCl3) delta 3.4 (s, 3H), 7.75 (s, IH).

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 6299-25-8, 4,6-Dichloro-2-(methylthio)pyrimidine.

Reference:
Patent; CURIS, INC.; WO2009/86012; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 799842-07-2, 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 799842-07-2 as follows.

General procedure: Aq 1 M NaOH (9 mL, 1.5 equiv) was added to a stirred MeOH (20mL) solution of the appropriate aromatic thiol (7.2 mmol, 1.2equiv). The solution was stirred at r.t. for 15 min and then the heterocyclicalkyl bromide 2 or 3 (6 mmol, 1 equiv) was added. When rosuvastatin moiety bromides 2 were used, THF (10 mL) was also added to the mixture to improve solubility. After 18 h, the solvent was evaporated, the residue was dissolved in CH2Cl2 (50 mL), and washed with H2O (100 mL). The aqueous phase was additionally extracted with CH2Cl2 (2 ¡Á 25 mL). The combined organic phases were dried (MgSO4) and the solvent was evaporated. The residuewas recrystallized and the isolated product was dried in vacuumovernight at 60 C below 50 mbar to give the pure sulfide heterocyclic precursor 4 or 5 in 75-97% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,799842-07-2, its application will become more common.

Reference:
Article; Fabris, Jan; ?asar, Zdenko; Smilovi?, Ivana Gazi?; ?rnugelj, Martin; Synthesis; vol. 46; 17; (2014); p. 2333 – 2346;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 7752-82-1 , The common heterocyclic compound, 7752-82-1, name is 5-Bromopyrimidin-2-amine, molecular formula is C4H4BrN3, 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.

To a solution of 2-amino pyridine (30 g, 0.31 mol) in DME (120 mL) was added chloro acetone (40.5 mL, 0.47 mol) at room temperature. The reaction mixture was heated to reflux, and then stirred for 48 hours. The volatiles were concentrated under reduced pressure. Then the residue was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-2 (20 g, 48%) as a liquid. Mass (m/z): 133 [M++1]. 1H NMR (200 MHz, dmso-d6): delta8.05 (d, J=8.2 Hz, 1H), 7.35 (s, 1H), 7.1 (t, J=6.8 Hz, 1H), 6.7 (t, J=6.8 Hz, 1H), 6.5 (d, J=8.2 Hz, 1H), 2.45 (s, 3H). To a solution of Int-2 (10 g, 76.7 mmol) in acetonitrile (50 mL) was added N-iodo succinamide (20.4 g, 80 mmol) portion wise at room temperature and then stirred for 48 hours. The precipitated solid was filtered off. The crude material was re-crystallized from ethyl acetate/water to afford Int-3 (9 g, 49%) as solid. Mass (m/z): 259 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.22 (d, J=8 Hz, 1H), 7.47 (d, J=7.2 Hz, 1H), 7.29 (t, J=7.0 Hz, 1H), 2.35 (s, 3H). To a solution of Int-3 (6.0 g, 29.2 mmol) in IPA-H2O (75 mL, 2:1) was added PdCl2(dppf).DCM (4.7 g, 5.8 mmol), followed by the addition of tert-butyl amine (3.1 g, 43.8 mmol) at room temperature and the resulting reaction mixture was degassed for 15 minutes. Then Int-4 (2.9 g, 18.6 mmol) was added to the reaction mixture at room temperature. The reaction mixture was heated to 100 C. and then stirred for 16 hours. The reaction mixture was diluted with water (100 mL), extracted with EtOAc (3¡Á100 mL), washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure. The crude material was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-5 (1.6 g, 28%). Mass (m/z): 244 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.51 (t, J=5 Hz, 2H), 7.71 (s, 1H), 7.63-7.55 (m, 2H), 7.34 (t, J=7 Hz, 1H), 6.94 (t, J=7 Hz, 1H), 2.43 (s, 3H). To a stirred mixture of 5-bromo 2-aminopyrimidine (8 g, 45.97 mmol) in MeOH-CH3CN (200 mL) in a steel bomb were added Pd(CH3CN)2Cl (2.38 g, 9.19 mmol), racemic-BINAP (5.7 g, 9.19 mmol), DIPEA (10.4 mL, 53.7 mmol) at room temperature and then closed the steel vessel tightly. Then CO gas (100 psi) was purged into the steel bomb and the stirring was continued at 120 C. for 45 hours. The reaction mixture was allowed to room temperature. The reaction mixture was filtered through a pad of celite. The celite pad was washed with excess of methanol and the filtrate was concentrated under vacuum. The crude material was purified by column chromatography eluting with 0.75% MeOH/DCM to afford Int-6 (5 g, 71%) as solid. Mass (m/z): 154 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.65 (s, 3H), 7.49 (brs, 2H), 3.58 (s, 3H) To a stirred mixture of Int-5 (3 g, 2.34 mmol) and Int-6 (1.8 g, 12.34 mmol) in 1,4-dioxane (90 mL) were added Pd(OAc)2 (279 mg, 1.23 mmol) and Xanthpos (710 mg, 1.23 mmol) followed by cesium carbonate (6 g, 18.5 mmol) at room temperature. The resulting mixture was degassed and stirred at reflux temperature for 30 hours. The reaction mixture was cooled to room temperature and then stirred for 15 minutes. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum. The crude material was purified by column chromatography eluting with 1.5% MeOH/DCM to afford Int-7 (0.6 g, 13.6%) as solid. Mass (m/z): 361.2 [M++1]. 1H NMR (500 MHz, dmso-d6): delta 10.76 (brs, 1H), 8.97 (s, 2H), 8.56 (d, J=7, 1H), 8.47 (d, J=5.5 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.5 Hz 1H), 7.34-7.29 (m, 2H), 6.99 (t, J=76 Hz, 1H), 3.84 (s, 3H), 2.46 (s, 3H). To a stirred solution of Int-7 (0.5 g, 1.38 mmol) in MeOH-CH3CN (1:2, 25 mL) was added aqueous NH2OH solution (15 mL) at 0 C. After being stirred for 20 minutes at the same temperature, NaOH (0.44 g, 11.10 mmol) in water (1 mL) was added drop wise to the reaction mixture at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 days. The volatiles were concentrated under vacuum and the obtained residue was diluted with water and neutralized to about pH 7 with 2 N HCl at 0 C. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum to afford the title compound (0.4 g, 80%) as off-white solid. Mass (m/z): 362.1 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 11.2 (bs, 1H), 10.5 (s, 1H), 9.12 (bs, 1H), 8.84 (s, 2H), 8.57 (d, J=7.0 Hz, 1H), 8.45 (d, J=5.0 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.0 Hz, 1H), 7.32 (t, J=7.5 Hz, 1H), 7.25 (d, J=4.0 Hz, 1H), 6.98 (d, J=7.0 Hz, 1H), 2.49 (s, 3H). 13C NMR (125 MHz, dmso-d6): delta 160.7, 157.1, 153.0, 148.7, 144.5, 142.3, 137.9, 125.2, 123.9, 118.8, 118.2, 117.0, 116.6, 112.7, 112.4, 14.3.

The synthetic route of 7752-82-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Melvin, JR., Lawrence S.; Graupe, Michael; Venkataramani, Chandrasekar; US2010/29638; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4316-93-2, Adding some certain compound to certain chemical reactions, such as: 4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine,molecular formula is C4HCl2N3O2, 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 4316-93-2.

6-Chloro-5-nitropyrimidin-4-amine[00161] A solution of 28% aqueous ammonium hydroxide (670 mL, 5.35 mol, 1.04 equiv) was added in a drop-wise fashion to a rapidly stirred solution of the 4,6-dichloro-5- nitropyrimidine solid (1000 g, 5.16 mol, 1.00 equiv) in diethyl ether (4000 mL) and methanol (670 mL). The addition was carried out over a period of 2 hours. Upon completion of addition, the resulting yellow solid was filtered off, washed with water and hexane, and dried under reduced pressure to give the title compound as a yellow solid (yield: 675 g). This crude solid was used in the next step without any further purification. NMR (400 MHz, DMSO- d6): delta 8.97 (s, 1H), 7.91 (broad s, 2H). MS (EI) for C4H3CIN4O2: 175 (MH+).

According to the analysis of related databases, 4316-93-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; PATRICK, Kearney; WO2012/37226; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 171887-03-9, Adding some certain compound to certain chemical reactions, such as: 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide,molecular formula is C5H4Cl2N4O, 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 171887-03-9.

7-Chloro-3-r6-ri-hvdroxy-l-methylethyl1pyridine-2-ylmethyl)-3H-ri,2,31triazolor4.5- Patent; VERNALIS (R&D) LIMITED; WO2009/156737; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia