Pyrimidines

Synthetic Route of 862730-04-9, Adding some certain compound to certain chemical reactions, such as: 862730-04-9, name is 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine,molecular formula is C8H10IN5, 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 862730-04-9.

Synthesis of 4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluorophenol (BA59); A solution of 3-fluoro-4-hydroxyphenylboronic acid (103 mg, 0.66 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (100 mg, 0.33 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 using silica gel column chromatography [MeOH-CH2Cl2, 2:98] to yield BA59 (26 mg, 27% yield). ESI-MS (M+H)+ m/z calcd 288, found 288.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 862730-04-9, 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 355806-00-7, 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 355806-00-7, name is (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl) methylamino]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid tert-butyl ester. This compound has unique chemical properties. The synthetic route is as follows.

Example 7; General procedure for preparing isolated ammonium salts of rosuvastatin; 5 g of terf-butyl ester of rosuvastatin 1.75 ml of 8 M NaOH 25 ml of demineralized water 10 ml of tetrahydrofuran EPO The reactants and the solvents are stirred from 50 to 55C for 1 hour. The solution formed is then allowed to cool to room temperature and washed with 50 ml methylcyclohexane yielding 33 ml of aqueous solution of sodium salt of rosuvastatin.To 33 ml of sodium rosuvastatinate solution prepared in the above described experiment is added 1.3 ml 85% phosphoric acid, previously dissolved in 5 ml of water. Reaction mixture is extracted with 40 ml of /so-butyl acetate. Organic layer is separated off and dried with 5 g of anhydrous magnesium sulphate. Drying agent is filtered off and washed with 10 ml /so-butyl acetate obtaining 52 ml of filtrate containing rosuvastatinic acid, which is divided into smaller portions for preparing various ammonium salts.To 5 ml of the obtained solution 1.5 equivalents of appropriate amine and 5 ml tert-butyl methyl ether are added. Rosuvastatin substituted ammonium salt is filtered off and dried on filter. The following solid salts are prepared:cyclohexylammonium salt of rosuvastatin: 0.45 g, 99.71% area by HPLC;1H-NMR: (CD3OD): 1.10 – 1.45 (12H,m), 1.31 (6H,d, J=7Hz), 1.48 – 1.56 (1H,m), 1.62 – 1.72 (1 H,m), 1.80 – 1.87 (2H,m), 1.97 – 2.03 (2H,m), 2.25 (1H,dd, J1=MHz, J2=7.6Hz), 2.34 (1H,dd, J1=MHz1 J2=4.9Hz), 2.98 – 3.09 (1 H,m), 3.51 (1H,h, J=7Hz), 3.52 (3H,s), 3.54 (3H,s), 3.92 – 3.97 (1H,m), 4.33 – 4.40 (1H,m), 5.56 (1 H,dd, J1=^Hz, J2=6Hz), 6.62 (1H,dd, J1=^Hz, J2=1.2Hz), 7.14 – 7.22 (2H,m), 7.69 – 7.75 (1H,m);dicyclohexylammonim salt of rosuvastatin: 0.35 g, 99.82% area;1H-NMR: (CD3OD): 1.12 – 1.76 (20H,m), 1.29 (d, J=7Hz), 1.48 – 1.56 (1H,m), 1.62 – 1.72 (1H,m), 1.83 – 1.92 (4H,m), 2.01 – 2.09(4H,m), 2.25 (1H,dd, J1=HHz, J2=7,6Hz), 2.34 (1H,dd, J1=MHz, J2=4.9Hz), 3.07 – 3.17 (2H,m), 3.51 (1H,h, J=7Hz), 3.52 (3H,s), 3.54 (3H,s), 3.92 – 3.97 (1H,m), 4.33 – 4.40 (1H,m), 5.56 (1H,dd, J1=IeHz, J2=6Hz), 6.62 (1H,dd, J,=16Hz, J2=1.2Hz), 7.14 – 7.22 (2H,m), 7.69 – 7,75 (2H,m);pyrrolidinium salt of rosuvastatin: 0.28 g, 99.71% area,1H-NMR: (CD3OD): 1.29 (6H,d, J=7Hz), 1.48 – 1.56 (1H,m), 1.62 – 1.72 (1H,m), 1.96 – 2.01 (4H,m), 2.25 (1H,dd, J1=MHz, J2=7,6Hz), 2.34 (1H,dd, J1=MHz, J2=4,9Hz), 3.20 – 3.25 (4H,m), 3,51 (1H,h, J=7Hz), 3.52 (3H,s), 3.54 (3H,s), 3.92 – 3.97 (1 H,m), 4.33 – 4.40 EPO (1 H,m), 5.56 (1H,dd, J1=IeHz, J2=6Hz), 6.62 (1 H,dd, J1=IeHz, J2=1 ,2Hz), 7.14 – 7.22 (2H,m), 7.69 – 7.75 (2H,m);piperidinium salt of rosuvastatin: 0.28 g, 99.77% area;1H-NMR: (CD3OD): 1.29 (6H,d, J=7Hz), 1.48 – 1.56 (1H,m), 1.62 – 1.81 (7H,m), 2.25 (1 H,dd, J1=MHz, J2=7.6Hz), 2,34 (1 H,dd, J1=MHz, J2=4,9Hz), 3.09 – 3.13 (4H,m), 3.51 (1 H,h, J=7Hz), 3.52 (3H,s), 3.54 (3H,s), 3.92 – 3.97 (1H,m), 4.33 – 4.40 (1 H,m), 5.56 (1 H,dd, J1=IeHz, J2=6Hz), 6.62 (1H,dd, J1=^Hz, J2=1.2Hz), 7.14 – 7,22 (1H,m), 7.69 – 7.75 (2H,m);morpholinium salt of rosuvastatin: 0.30 g, 99.51% area;1H-NMR: (CD3OD): 1.29 (6H,d, J=7Hz), 1.49 – 1.57 (1 H,m), 1.62 – 1.72 (1H,m), 2.25 (1 H,dd, J1=MHz, J2=7.6Hz), 2.34 (1 H,dd, J1=HHz, J2=4.9Hz), 3.12 – 3.16 (4H,m), 3.51 (1 H,h, J=7Hz), 3.52 (3H,s), 3.53 (3H,s), 3.81 – 3.,85 (4H,m), 3.92 – 4.00 (1H,m), 4.33 – 4.40 (1H,m), 5.57 (1H,dd, J1=IeHz, J2=6Hz), 6.62 (1H,dd, J1=IeHz, J2=1.2Hz), 7.14 – 7.22 (2H,m), 7.69 – 7.75 (1H,m);1-adamantylammonium salt of rosuvastatin: 0.66 g, 99.75% area;1H-NMR: (CD3OD): 1.29 (6H,d, J=7Hz), 1.48 – 1.56 (1H,m), 1.62 – 1.85 (16H,m), 2.15 (3H,s (broad)), 2.25 (1 H,dd, J1=HHz, J2=7,6Hz), 2.34 (1H,dd, J1=UHz, J2=4.9Hz), 3.51 (1 H,h, J=7Hz), 3.52 (3H,s), 3.54 (3H,s), 3.92 – 3.97 (1H,m), 4.33 – 4.40 (1 H,m), 5.56 (1H,dd, J1=IeHz, J2=6Hz), 6.62 (1 H,dd, J1=^Hz, J2=1.2Hz), 7.14 – 7.22 (2H,m), 7.69 – 7.75 (1 H,m).; Example 8; Preparation of N-cyclohexylammonium salt of rosuvastatin; 1O g tert-butyl ester of rosuvastatin3.5 ml 8 M NaOH50 ml demineralized water20 ml tetrahydrofuran EPO The reactants and the solvents are stirred from 50 to 55C for 1 hour. The solution formed is then allowed to cool to room temperature and washed with 100 ml methylcyclohexane yielding 66 ml of aqueous solution of sodium rosuvastatinate.To 33 ml of the obtained solution is added 1.3 ml 85% phosphoric acid in 5 ml demineralized water. Rosuvastatinic acid is extracted with 40 ml /so-propyl acetate. 4.7 g of anhydrous magnesium sulphate and 0.5 g charcoal is added to organic phase and suspension is stirred for 45 min. Magnesium sulphate and charcoal are filtered off yielding 41 ml of filtrate.16 ml of the filtrate is separated and treated by addition of 0.5 ml of cyclohexylamine in 8 ml of /so-propyl acetate during stirring and rosuvastatin cyclohexylammonium salt precipitate instantaneously as white solid. It is separated by filtration, precipitate is washed on the filter with 10 ml of /so-propyl acetate and dried on the filter yielding 1.34 g of the de…

According to the analysis of related databases, 355806-00-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2006/136407; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2134-38-5, Adding some certain compound to certain chemical reactions, such as: 2134-38-5, name is Ethyl 2-methylpyrimidine-5-carboxylate,molecular formula is C8H10N2O2, 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 2134-38-5.

Step 2: Preparation of N-(4-chloro-6-(ethylamino)pyrimidin-5-yl)-2-methylpyrimidine-5- carboxamide.To a mixture of 6-chloro-N4-ethylpyrimidine-4,5 -diamine (16 g, 91 mmol) and ethyl -2- methylpyrimidine-5-carboxylate (15 g, 90 mmol) in 50 ml of dimethyl ether at RT, a slurry of sodium teri-butoxide (9.1 g, 92 mmol) in DME (25 ml) was added over the course of 1 min (reaction internal temperature rose to 43 C) . The reaction mixture was then stirred at RT for 2 h, after which it was quenched by the addition of water (75 ml) and EtOAc (75 ml). The reaction mixture was extracted with EtOAc (75 ml x 2). The aqueous layer was then charged with acetic acid (5.3 ml, 92 mmol) and a slurry formed. The solid was collected by filtration, then washed with 75 ml of 1 : 1 DME : water, after which it was dried under vacuum at 35 C for 16 h to provide N-(4-chloro-6-(ethylamino)pyrimidin-5-yl)-2- methylpyrimidine-5-carboxamide. MS (ESI) Calc’d for Ci2Hi4ClN60 [M+H]+: 293, found: 293.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 2134-38-5, Ethyl 2-methylpyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; FONG, Kin Chiu; ANTHONY, Neville John; ZHOU, Hua; KATZ, Jason D.; YANG, Lihu; LI, Chaomin; TIAN, Yuan; MU, Changwei (Charles); YE, Baijun; SHI, Feng; ZHAO, Xiaoli; FU, Jianmin; WO2015/188369; (2015); 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. 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine, molecular formula is C6H6N4, 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. Product Details of 2227-98-7

[0035] Example A. Synthesis of 2-[({4-amino-5H-pyrrolo[3,2-d]pyrimidin-7- yljmethyl) amino] ethan-l-ol (A.1). (0059) (0060) [0036] 2-[ ({4-Amino-5H-pyrrolo[3, 2-dJpyrimidin- 7-yl }methyl) amino] ethan-l-ol (A.1). 2-Aminoethanol (0.099 mL, 1.64 mmol), 9-deazaadenine (0.220 g, 1.64 mmol) and aq. formaldehyde solution (37%, 0.15 mL, 1.99 mmol) were stirred together in tert-butanol (3 mL) at 70 C for 16 h. Silica gel was added to absorb all the solvent then the solvent was evaporated and the residue purified by chromatography on silica gel (CHCl3-MeOH-28% aq.NH4OH, 70:25:5). Fractions containing product were evaporated and the residue chromatographed again on silica gel (2-PrOH-28% aq. NH4OH, 92:8) to give A.1 as a colourless solid (0.101 g, 30%). NMR (500 MHz, CD3OD): delta 8.16 (s, 1H), 7.47 (s, 1H), 3.95 (s, 2H), 3.68 (t, J = 5.6 Hz, 2H), 2.78 (t, J = 5.6 Hz, 2H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 152.1 (C), 150.9 (CH), 146.6 (C), 129.0 (CH), 1 15.4 (C), 114.4 (C), 61.6 (CH2), 51.6 (CH2), 43.4 (CH2). ESI-HRMS calcd for C9H14N50+, (M+H) 208.1 193, found 208.1 192.

With the rapid development of chemical substances, we look forward to future research findings about 2227-98-7.

Reference:
Patent; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; SCHRAMM, Vern, L.; CLINCH, Keith; GULAB, Shivali, Ashwin; WO2015/123101; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3680-69-1, 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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, 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.

Step 1To a solution of 4-chloro-7H-pyrro]o[2,3-d]pyrimidine (8.0 g , 52.32 mmol, 1.0 eq) in DMF (40 raL), NiS ( 15.7g , 57.55 mmol, 1.1 eq) was added at 0 C. The reaction mixture was stirred overnight at room temperature. Water (40 rnL) was added to the reaction mixture, extracted with EtOAc. The organic layer was dried over Na2S04 and concentrated under vacuum to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (14.6 g, 100 % in yield).

According to the analysis of related databases, 3680-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; WO2012/158795; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 14080-23-0, Adding some certain compound to certain chemical reactions, such as: 14080-23-0, name is 2-Cyanopyrimidine,molecular formula is C5H3N3, 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 14080-23-0.

To the flask was added 0.10g of 2cyanopyrimidine,12% by mass aqueous sodium hydroxide solution 13mL was stirred at 70 30 minutes. Of 1N dilutehydrochloric acid to pH ~ 3 by adding little by little and, by concentration of the resulting organic layer was extracted three times with 10mL of ethyl acetate, to give0.10g of Compound A218

According to the analysis of related databases, 14080-23-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG CHEMICAL CO., LTD; PARK, JONG HO; SAH, KONG CHUN; KIM, SUNG HYUN; BAEK, GYUNG LIM; RYU, CHANG HYUN; (91 pag.)KR2015/128789; (2015); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1032452-86-0, 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 1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl p-aminobenzoate hydrochloride (4.24 g, 22.60 mmol) and p-toluenesulfonicacid (3.90 g, 22.60 mmol) in 1, 4-dioxane (80 mL) was added 1 (5.0 g, 20.52 mmol). The reaction wasmonitored by TLC and stirred at 85 C for 3 h. After cooling to room temperature, 6 mL of ammoniawater was added dropwise followed by addition of 80 mL of H2O. The mixture was stirred at roomtemperature overnight with the resulting precipitate being filtered. The filter residue was washed withwater and dried to give compound 2 (5.85 g, yield: 79%) as an orange-yellow solid, which was usedin the following reaction without further purification. 1H NMR (600 MHz, DMSO-d6) delta 9.85 (s, 1H),8.61 (d, J = 8.1 Hz, 1H), 8.42 (d, J = 5.3 Hz, 1H), 8.34 (s, 1H), 8.02 (d, J = 8.4 Hz, 2H), 7.93 (d, J = 8.4 Hz,2H), 7.56 (d, J = 8.3 Hz, 1H), 7.33-7.28 (m, 2H), 7.24 (t, J = 7.5 Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H).

According to the analysis of related databases, 1032452-86-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dong, Hang; Yin, Hao; Zhao, Chunlong; Cao, Jiangying; Xu, Wenfang; Zhang, Yingjie; Molecules; vol. 24; 13; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 46155-89-9, 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 46155-89-9, name is 1,3-Dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 111 5-[4-(4-Chlorobenzoyl)benzyl]-1,3-dimethylpyrrolo [3,2-d]pyrimidine-2,4-dione To a solution of 1,3-dimethylpyrrolo[3,2-d]-pyrimidine-2,4-dione (0.402 g, 2.24 mmol) and 4-(4-chlorobenzoyl) benzyl bromide (1.20 g, 3.88 mmol) in DMF (5 ml) was added potassium carbonate (0.73 g, 5.28 mmol) and the mixture was stirred at 60 C. for 2 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developer: isopropyl ether: ethyl acetate: methylene chloride=2:1:1) and recrystallized from ethyl acetate to provide colorless needles. 0.360 g (39%) 1 H-NMR (CDCl3) delta: 3.40(3H,s), 3.49(3H,s), 5.66(2H,s), 6.00(1H,d,J=3.0 Hz), 7.01(1H,d,J=3.0 Hz), 7.29(2H,d,J=8.6 Hz), 7.45(2H,d,J=8.6 Hz), 7.72(2H,d,J=8.6 Hz),,7.73(2H,d,J=8.6 Hz). IR (KBr): 1693, 1653, 1549, 1466, 1434, 1406, 1267, 1065, 1016, 962, 922, 856, 744, 669, 503 cm-1.

According to the analysis of related databases, 46155-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5753664; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 89793-12-4, 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. 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

Step 1: A mixture of ethyl 2-chloropyrimidine-5-carboxylate (1.86 g, 10 mmol), compound 1 (4-amino-l-Boc-piperidine, 3.00 g, 15 mmol), and NEt3 (3.0 g, 30 mmol) in 1,4-dioxane (20 mL) was stirred at 95°C overnight. The mixture was concentrated, and EA (60mL) and aqueous citric acid (60 mL) were added to the mixture followed by stirring the mixture for 30 min. The organic layer was collected, dried and concentrated to get compound 2 (3.4 g, yield: 97percent) as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89793-12-4, Ethyl 2-chloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; SHEARSTONE, Jeffrey, R.; JARPE, Matthew, B.; (152 pag.)WO2016/57779; (2016); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-63-6, 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. 22536-63-6, name is 2-Chloro-4-methoxypyrimidine, molecular formula is C5H5ClN2O, 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.

To a solution of cis-1-(3-methoxyphenyl)-4-piperazin-1-ylcyclohexanecarbonitrile dihydrochloride (50 mg, 0.134 mmol), triethylamine (0.0654 ml, 0.469 mmol) and potassium carbonate (92.6 mg, 0.670 mmol) in N,N-dimethylformamide (DMF, 1.5 mL), 2-chloro-4-methoxypyrimidine (29.1 mg, 0.201 mmol) was added at room temperature, and then the mixture was heated to 70C and stirred for 5 hours. Water was added thereto to quench the reaction, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water twice, dried over anhydrous magnesium sulfate, filtrated, and the solvent was removed from the filtrate in vacuo. The residue was purified by silica gel chromatography to give 39.3 mg of the title compound as a white crystal. High-performance liquid chromatography/mass spectrometry m/z 408.4 (M+H) Retention time: 2.36 min.

According to the analysis of related databases, 22536-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1679069; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia