Pyrimidines

Application of 4359-87-9, 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. 4359-87-9, name is 2,4,6-Trichloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

Reference Example 1: N,N-dibenzyl-N’-tert-butyl-2-chloro-5-nitropyrimidine-4,6-diamine To 2,4,6-trichloro-5-nitropyrimidine (, 22.8 g) in methylene chloride(l 70 mL), a solution of tert-butylamine (7.3 g) in methylene chloride (30 mL) was slowly added dropwise at 0 C. To the reaction mixture, diisopropylethylamine (17.3 mL) was slowly added dropwise at 0 C. The reaction mixture was stirred at 0 C for 60 minutes. To the reaction mixture, water was poured and the reaction mixture was extracted with methylene chloride. The obtained organic layer was washed with a saturated saline solution, and was dried over sodium sulfate, and thereafter, was concentrated under a reduced pressure. 12.7 g of the obtained intermediate (27.8 g) was dissolved in methylene chloride (170 mL). To the solution, a solution of dibenzylamine (19.2 mL) in methylene chloride (30 mL) was added dropwise at 0 C. To the reaction mixture, diisopropylethylamine (17.3 mL) was added dropwise at 0 C. The reaction mixture was stirred at 0 C for 60 minutes. To the reaction mixture, water was poured and the reaction mixture was extracted with methylene chloride. The obtained organic layer was washed with a saturated saline solution, and was dried over sodium sulfate, and thereafter, was concentrated under a reduced pressure. The remaining intermediate (15.09 g) was similarly reacted. The obtained crude product was purified by silica gel column chromatography to give the title compound (27.2 g) having the following physical properties. TLC: Rf 0.45 (hexane: ethyl acetate = 9 : 1); 1H-NMR (CDCl3): delta1.51, 4.52, 7.06-7.14, 7.23-7.38, 8.41.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4359-87-9, its application will become more common.

Reference:
Patent; Ono Pharmaceutical Co., Ltd.; YAMAMOTO, Shingo; KURONO, Masakuni; YOSHIDA, Atsushi; HOTTA, Shingo; (53 pag.)EP3560926; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 947533-45-1, 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 947533-45-1, name is 2-bromo-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Intermediate 4033A (100 mg, 0.180 mmol), 2-bromo-5-fluoropyrimidine (Frontier) (48 mg, 0.27 mmol, 1 .5 eq), potassium carbonate (87 mg, 0.63 mmol, 3.5 eq) and bis(tri-t- butylphosphine)palladium (0) (18 mg, 0.036 mmol, 0.20 eq) are charged in a microwave vial and DMF (1 .5 ml.) and water (0.50 ml.) are added. The vial is purged with argon, sealed and warmed in a microwave oven at 125 C for 10 min. The reaction mixture is filtered and purified by preparative HPLC to provide compound 4033 (tR: 1 .92, (M+H)+: 539.3/541 .3).

According to the analysis of related databases, 947533-45-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1146629-75-5, 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 1146629-75-5, name is (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate. This compound has unique chemical properties. The synthetic route is as follows.

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).According to this procedure, but starting from tert-butyl 2-(5-chloro-2-ethyl phenyl)-4-iodo-1 H-pyrrole-1 -carboxylate, using 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl 2,2-dimethylpropanoate instead of 6-iodopyrimidin-4-amine in the step 16 and removing the 2,2-dimethylpropanoyl protecting group with LiOH.H20 in THE/water at roomtemperature, the following compound was prepared:2-(5-Chloro-2-ethylphenyl)-N-methyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yI)-1 H-pyrrole-1 -carboxamide (compd185)ESI (+) MS: m/z 380 (MW).

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 1146629-75-5, (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate.

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

Electric Literature of 2915-16-4, 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. 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. A new synthetic method of this compound is introduced below.

Under a nitrogen atmosphere, 50g (187mmol) the compound 2-chloro-4,6-diphenyl pyrimidine was dissolved in 1LTHF added thereto 37g (155mmol) (3- bromophenyl) borate, and 2.1g (1.8mmol) tetrakis (triphenylphosphine) palladium, and the mixture was stirred. Subsequently, thereto added 64g (467mmol) of potassium carbonate saturated aqueous solution, and the resulting mixture was heated at reflux for 80 12 hours. When the reaction was completed, water was added to the reaction solution, and the mixture was extracted with dichloromethane ((the DCM), followed by removal of water and dried over anhydrous MgSO4 filtered and concentrated under reduced pressure. The residue obtained was separated via flash column and chromatography to obtain 66g (92%) compound I-17.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2915-16-4, 2-Chloro-4,6-diphenylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Samsung SDI Co., Ltd.; Jin, Chengxuan; Jin, Yongquan; Liu, Dongwan; Jin, Lunhuan; Liu, Yinshan; Zheng, Chengxian; (85 pag.)CN105566200; (2016); A;,
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. 28969-60-0, name is 2,5,6-Trichloropyrimidin-4-amine, molecular formula is C4H2Cl3N3, 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. Formula: C4H2Cl3N3

EXAMPLE 1 This example illustrates the preparation of 4(2,3,5,6-tetrafluoro-4-trifluoromethylanilino)2,5,6-trichloropyrimidine (Comound No. 6 of Table I) having the formula: SPC1 4-Amino-2,5,6-trichloropyrimidine (1.98 g) was dissolved in dry dimethylformamide (25 cc) and the solution added dropwise to a stirred suspension of sodium hydride (0.5 g) in dry dimethylformamide (25 cc) under a nitrogen atmosphere at 0C. When the addition was complete and evolution of hydrogen had ceased a solution of octafluorotoluene (2.4 g) in dry dimethylformamide (15 cc) was added dropwise to the mixture at 0C. When this addition was complete the mixture was stirred for 30 minutes, and the temperature allowed to rise to 21C. The mixture was then poured into a mixture of iced water and salt (400 cc) and acidified with dilute hydrochloric acid. The gummy precipitate which was formed slowly hardened on standing (18 hours) and was twice recrystallized from a mixture of methylene chloride and petroleum ether (boiling range 40-60C) to yield 4(2,3,5,6-tetrafluoro-4-trifluoromethylanilino)-2,5,6-trichloropyrimidine, having a melting point of 152.4 to 153C.

With the rapid development of chemical substances, we look forward to future research findings about 28969-60-0.

Reference:
Patent; Imperial Chemical Industries Limited; US3974276; (1976); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 49845-33-2, 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. 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

2,4-dichloro-5-nitropyrimidine(3g, 15.4 mmol) was dissolved in tetrahydrofuran(52 mL) and 2N methylamine (15.4 mL) dissolved in tetrahydrofuran was slowly added at -78°C. The resulting solution was stirred for 10 minutes and then further stirred for 50 minutes at room temperature. The resulting solution was concentrated under reduced pressure, diluted with ethyl acetate(50 mL), and washed with water (30 mL) and saline (30 mL). The resultant was dehydrated with anhydrous sodium sulfate, concentrated under reduced pressure, and applied to column chromatography (EA : Hex = 20 : 1 ? 5 : 1) to yield Compound XL (925 mg (32percent)). 1H NMR (600MHz, chloroform-d1) delta 9.05(s, 1H), 8.41(br, 1H), 3.23 (d, J = 4.8Hz, 3H),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,49845-33-2, 2,4-Dichloro-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; LegoChem Biosciences, Inc.; CHO, Young Lag; YUN, Joung Yul; PARK, Chul Soon; CHAE, Sang Eun; LEE, Hyang Sook; OH, Kyuman; HEO, Hye Jin; KANG, Dae Hyuck; YANG, Young Jae; KWON, Hyun Jin; PARK, Tae Kyo; WOO, Sung Ho; KIM, Yong Zu; EP2706062; (2014); A2;,
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. 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, molecular formula is C6H4Cl2N2OS, 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: C6H4Cl2N2OS

Step 2. Preparation of 4-Chloro-6-methylsulfanyl-]H-pyrazolo[3,4-d]pyrimidine 4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (7.54 g, 0.0338 mol) was added to 80 mL of dioxane and stirred for 10 minutes at room temperature. Diisopropyl ethylamine (6.03 mL, 0.0340 mol) was added and the mixture was cooled in an ice bath with stirring for 10 minutes. Anhydrous hydrazine (1.08 mL, 0.0338 mmol) was added dropwise over three minutes, and stirring was continued for an additional five minutes. The ice bath was removed, and the reaction ixture was heated to reflux with stirring for two hours. The reaction mixture was then stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added to 20 mL of 2 N HCl and 100 mL EtOAc. The resulting suspension was stirred and filtered, ad the solid was washed with water followed by EtOAc. The organic phase of the filtrate was collected, and the aqueous phase was extracted three times with 150 mL EtOAc. The combined organic phases were dried (MgSO4), filtered, and the filtrate was evaporated under reduced pressure. The resulting solid was washed with diethyl ether/hexanes (1:1) and the solid was dried to provide 3.13 g of crude 4-Chloro-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine. Mass Spec. M+H =201.

With the rapid development of chemical substances, we look forward to future research findings about 33097-11-9.

Reference:
Patent; Arora, Nidhi; Billedeau, Roland Joseph; Dewdney, Nolan James; Gabriel, Tobias; Goldstein, David Michael; O’Yang, Counde; Soth, Michael; US2005/197340; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 17321-93-6 ,Some common heterocyclic compound, 17321-93-6, molecular formula is C5H6BrN3, 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.

A mixture of 5-bromo-4-methylpyrimidine-2-ylamine (5.0g, 26 mmol), potassium acetate (7.83g, 79.8 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 1,3,2- dioxaborolane (7.43 g, 29.2 mmol) in dioxane (140 mL) was stirred for 20 min under nitrogen. 1, 1 ‘-bis (diphenylphosphino) ferrocene palladium (II) chloride dichloromethane adduct (1.08 g, 1.33 mmol) was added to the reaction mixture. The reaction mixture was heated to 115 °C for 18 h under nitrogen. Upon completion, the mixture was cooled and EtOAc was added. The resulting mixture was sonicated and filtered. Additional EtOAc was used to wash the solid. The combined organic extracts were washed with water, dried over MgS04, filtered and concentrated. The crude was purified by chromatography eluting with 20-100percent EtO Ac/hex ane to yield 4.5 g of 4-methyl-5-(4,4,5,5-tetramethyl (l,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine (yield: 74percent). 1H-NMR (DMSO, 400 MHz): delta 8.28 (s, 1H), 6.86 (br s, 2H), 2.35 (s, 3 H), 1.25 (s, 12 H). MS (ESI) m/e (M+H+) 236.15, 154.07.

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. 17321-93-6, 2-Amino-5-bromo-4-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA-ROCHE AG; DOTSON, Jennafer; HEALD, Robert Andrew; HEFFRON, Timothy; JONES, Graham Elgin; KRINTEL, Sussie Lerche; MCLEAN, Neville James; NDUBAKU, Chudi; OLIVERO, Alan G.; SALPHATI, Laurent; WANG, Lan; WEI, BinQing; WO2012/82997; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5604-46-6, Adding some certain compound to certain chemical reactions, such as: 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde,molecular formula is C5H3Cl2N3O, 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 5604-46-6.

Intermediate 30Ethyl 2-(2-amino-6-chloro-5-formylpyrimidin-4-ylthio)acetate To a stirred suspension of 2-amino-4,6-dichloropyrimidine-5-carbaldehyde (Intermediate 29, 10.66 g, 55.52 mmol) in ethanol (100 mL), triethylamine (8.51 mL, 61.07 mmol) and ethyl 2- mercaptoacetate (6.12 mL, 55.52 mmol) were added. The reaction mixture was stirred at room temperature for 3 h. The precipitate was collected by filtration and washed with water, then recrystallized from 2-propanol, and dried in vacuo to afford 12.6 grams of the title compound. Reference: Tumkevicius, S. et al., J. Heterocyclic Chem., 2006, 43, 1629-33. LC/MS (ES+)[(M+H)+]: 276, 278 for C9Hi0ClN3O3S. 1R NMR (300 MHz, d6-DMSO): 1.19 (t, 3H), 3.98 (s, 2H), 4.10 (q, 2H), 7.95 (s, IH), 8.25 (s, IH), 10.08 (s, IH).

According to the analysis of related databases, 5604-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/27732; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 696-82-2, 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. 696-82-2, name is 2,4,6-Trifluoropyrimidine, molecular formula is C4HF3N2, 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.

(1) 26.8 parts of 4,6-diaminobenzene-1,3-disulfonic acid (hereinafter referred to as m-bis disulfonic acid) was dissolved in 200 parts of water, With 10% sodium carbonate solution to adjust the pH to 6, the whole solution, and then added 13.5 parts of trifluoropyrimidine at a temperature of 15 C, a pH of 4 under conditions of condensation 4. 0h, bis End point, to obtain a condensation product;

According to the analysis of related databases, 696-82-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Demeike Chemical Co., Ltd.; Wang Xiaojun; (8 pag.)CN106398299; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia