Day: March 16, 2022

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.1211522-68-7, name is 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C6H4Cl2N4, molecular weight is 203.0288, as common compound, the synthetic route is as follows.Quality Control of 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine

To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211522-68-7, 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 29939-37-5, 4-Hydroxy-6-hydrazinylpyrimidine, 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, Product Details of 29939-37-5, blongs to pyrimidines compound. Product Details of 29939-37-5

PREPARATION 3phenylmethyl 4-chloro-1 ,5,7,8-tetrahydro-6/-/-pyrido[3′,4′:4,5]pyrrolo[2,3-c/]pyricarboxylateStep 1 . phenylmethyl 4-[(6-oxo-1 ,6-dihydro-4-pyrimidinyl)hydrazono]-1- piperidinecarboxylateA suspension of 6-hydrazino-4(1 H)-pyrimidinone (0.966 g, 7.66 mmol) in ethanol(20 mL) and phenylmethyl 4-oxo-1 -piperidinecarboxylate (2.68 g, 1 1 .49 mmol) were heated in a 76 C oil bath for 3 hours. The reaction mixture was cooled in an ice-water bath before the solids were collected by filtration and dried under high vacuum over night to afford phenylmethyl 4-[(6-oxo-1 ,6-dihydro-4-pyrimidinyl)hydrazono]-1- piperidinecarboxylate (1 .53 g, 58%) as white solid MS (m/z) 342.1 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29939-37-5, 4-Hydroxy-6-hydrazinylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAMMOND, Marlys; ZHAO, Yongdong; WO2011/56739; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1189973-29-2, 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 1189973-29-2, name is (1-(5-Bromopyrimidin-2-yl)piperidin-3-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Synthesis of {l-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidin-2- yl]piperidin-3-yl}methanol :; To a solution of [l-(5-bromopyrimidin-2-yl)piperidin-3-yl]methanol (0.5 g, 1.83 mmol) in 1,4 dioxane (25 mL) were added bispinacolatodiborane (0.46 g, 3.3 mmol), potassium acetate ( 0.53 g, 5.4 mmol) and Pd (dppf)Cl2 (0.14 g, 0.18 mmol) under argon at room temperature (~25 0C). The mixture was heated at 80-90 0C for about 6 hours. It was cooled to room temperature (-25 0C), concentrated under reduced pressure and then purified through filtering column using sintered funnel full of 230-400 mesh size silica gel. It was eluted with 50% ethyl acetate in hexane and concentrated to afford title compound (0.4 g). MS m/e 289.93 (MH+).

According to the analysis of related databases, 1189973-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2009/156966; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 99420-75-4, 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. 99420-75-4, name is 5-Methylpyrimidine-2-carboxylic acid, molecular formula is C6H6N2O2, 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.

(0648) To a solution of 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24 mmol) in DMF (72.4 mL) was added Nu,Omicron-dimethylhydroxylamine hydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to 0 C and 1-propanephosphonic acid cyclic anhydride, (50 wt. % solution in EtOAc, 9.21 mL, 14.48 mmol) was added droppwise. The mixture was allowed to warm to 23 C overnight. LCMS indicated complete conversion to product. The mixture was then diluted with water, extracted with CHC13:IPA (3: 1) and washed with brine and a saturated aqueous NaHCC solution. The mixture was dried over Na2S04 concentrated in vacuo, and purified by silica gelchromatograph (0-100% Heptane:EtOAc) to yield Example 57.11 (0.7 g, 3.86 mmol, 53 % yield). NMR (500 MHz, CDC13) delta 8.61 – 8.69 (m, 2 H) 3.61 – 3.79 (m, 3 H) 3.27 – 3.47 (m, 3 H) 2.34 – 2.45 (m, 3 -ESI (pos.) m/z: 182.2 (M+H)+

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 99420-75-4, 5-Methylpyrimidine-2-carboxylic acid.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul John; HARVEY, James S.; MA, Zhihua; SHARMA, Ankit; (281 pag.)WO2019/89335; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 886365-79-3 , The common heterocyclic compound, 886365-79-3, name is 5-Bromo-2-(2-methoxyethylamino)pyrimidine, molecular formula is C7H10BrN3O, 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.

Synthesis of 4-(4-{2-[(2-methoxyethyl)amino]pyrimidin-5-yl}phenyl)-N- [5-(2-methyl-l,3-thiazol-4-yl)pyridin-2-yl]tetrahydro-2H-pyran-4-carboxamide (example 207)To a solution of 1-105 (75 mg, 0.16 mmol), KOAc (157 mg, 1.6 mmol),PdCi2(dppf).CH2Ci2 (33 mg, 0.04 mmol) in dioxane (2.0 mL) at room temperature is added R-8 (115 mg, 0.46 mmol). The reaction mixture is heated at 100 C in a sealed tube for 16 hours. The reaction mixture is allowed to cool to room temperature, followed by the addition R-31 (88 mg, 0.38 mmol) in THF (2.0 mL), 20% Na2C03 solution (2.0 mL), and Pd(PPh3)4 (23 mg, 0.20 mmol). The reaction mixture is heated in the microwave at 120 C for 60 minutes, allowed to cool to room temperature, and partitioned between EtOAc and H20. The combined organics are washed with H20, dried with Na2S04, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-10% MeOH in EtOAc) to give the title compound 207 (36 mg).

The synthetic route of 886365-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 16097-60-2, 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. 16097-60-2, name is 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

Under an ice bath, add 2-amino-4-chloro-6-trifluoromethylpyrimidine (197.0 mg, 1.0 mmol), N-tert-butoxycarbonyl-1,3-propanediamine (208.8 mg, 1.2 mmol) , Dissolved in methanol (8.0 ml), and stirred at reflux overnight. The solvent was recovered under reduced pressure to obtain a residue, which was purified by silica gel column chromatography. PE: EA (5: 1-2: 1) was first used as eluent to obtain 1-36 as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16097-60-2, 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang University; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Liu Tao; Li Jia; Dong Xiaowu; Zhou Yubo; Hu Yongzhou; Wang Peipei; Jin Tingting; Liu Jieyu; Hu Xiaobei; (51 pag.)CN110872277; (2020); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 98138-75-1, 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 98138-75-1 as follows.

To 6-chloro-4-methoxy-1 H-pyrazolo[3,4-d]pyrimidine (2.45 g) dissolved in dry DMF (60 ml) was added N-iodosuccinimide (3.45 g) and the reaction mixture heated to 80C under stirring. After 3 h the reaction mixture was cooled to RT and the DMF removed by rotary evaporation. Water was added to the residue which was then extracted three times with tert-butyl methyl ether. The combined organic phases were washed with water and brine and dried over sodium sulfate, filtered and evaporated to afford 6-chloro-3-iodo-4-methoxy-1 H-pyrazolo[3,4-d]pyrinnidine as a brown solid. Yield: 4.13 g (100%). MS (ES+): m/e = 310.9 (M+H), chloro pattern

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98138-75-1, its application will become more common.

Reference:
Patent; SANOFI; NAZARE, Marc; HALLAND, Nis; SCHMIDT, Friedemann; KLEEMANN, Heinz-Werner; WEISS, Tilo; SAAS, Joachim; STRUEBING, Carsten; WO2014/140065; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 90856-77-2, 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 90856-77-2 as follows.

3.0 g (7.0 mmol) of Intermediate I-3-2 and 80 ml of toluene were added to a reactor, and then, 0.4 g (3.3 mmol) of 4,6-dimethylpyrimidin-5-amine, 0.1 g (0.5 mmol) of Pd(dba)2, 0.2 g (1.0 mmol) of P(tBu)3, and 0.95 g (9.9 mmol) of sodium butoxide were added thereto. The mixture was then heated and stirred under reflux at a temperature of 120 C. for 36 hours. When the reaction was completed, the resulting mixture was concentrated under reduced pressure, dissolved in dichloromethane, and filtered using diatomite. The organic layer obtained therefrom was dried by using magnesium sulfate to be distilled under reduced pressure, and purified by liquid chromatography to obtain 1.4 g (1.7 mmol, yield: 53%) of Intermediate I-3-1. LC-MS m/z=814 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90856-77-2, its application will become more common.

Reference:
Patent; Samsung Electronics Co., Ltd.; CHOI, Jongwon; ARATANI, Sukekazu; LEE, Kum Hee; LEE, Banglin; CHOI, Hyeonho; KWAK, Seungyeon; KWAK, Yoonhyun; KIM, Sangdong; KIM, Jiwhan; BAIK, Chul; CHO, Yongsuk; (115 pag.)US2019/74457; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 87253-62-1, Adding some certain compound to certain chemical reactions, such as: 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid,molecular formula is C8H8N4O2, 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 87253-62-1.

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

According to the analysis of related databases, 87253-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3974-16-1 , The common heterocyclic compound, 3974-16-1, name is 4,6-Dichloro-5-phenylpyrimidine, molecular formula is C10H6Cl2N2, 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.

C. Preparation of 4-chloro-6-(4-chlorophenyl)-5-phenylpyrimidine To a mixture of 4,6-dichloro-5-phenylpyrimidine (675 mg, 3.0 mmol), 4-chlorophenylboronic acid (704 mg, 4.5 mmol) and tetrakis(triphenylphosphine)palladium (173 mg, 0.15 mmol) in toluene (10 mL) at room temperature under argon was added aqueous Na2CO3 solution (2 M, 3 mL, 6 mmol). The resulting reaction mixture was stirred at 100 C. under argon for 5 h, after which time analysis by HPLC/MS indicated that the the reaction was complete. After cooling the reaction mixture to room temperature, water (15 mL) was added. The resulting mixture was extracted with EtOAc (2*25 mL). The combined organic layers were washed with saturated aqueous NaCl, then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluted with ethyl acetate-hexanes to obtain 571 mg of the title compound as a white solid. HPLC/MS: retention time=3.85 min, [M+H]30 =301.

The synthetic route of 3974-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wu, Gang; Mikkilineni, Amarendra B.; Sher, Philip M.; Murugesan, Natesan; Gu, Zhengxiang; US2006/287341; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia