Category: pyrimidines

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. 5767-35-1, name is 4-Chloro-6-hydrazinopyrimidine, molecular formula is C4H5ClN4, 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. COA of Formula: C4H5ClN4

General procedure: To s stirred suspension of the specific 1-(6-chloropyrimidin-4-yl)hydrazine (2) (3.0 mmol) inEtOH (20 mL) was added dropwise an appropriate aldehyde (3.6 mmol, 1.2 equiv) at r. t. over0.5-1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, thesolvent was removed under reduced pressure to afford the crude product. Purification by flashcolumn on silica gel furnished the corresponding pure hydrazone 3.

With the rapid development of chemical substances, we look forward to future research findings about 5767-35-1.

Reference:
Article; Tang, Caifei; Wang, Chao; Li, Zhiming; Wang, Quanrui; Synthesis; vol. 46; 20; (2014); p. 2734 – 2746;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 356058-42-9, name is 2-(2-((4-Fluorobenzyl)thio)-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetic acid. A new synthetic method of this compound is introduced below., Computed Properties of C16H15FN2O3S

Amine 8 (1 eq, 52 mg) and acid 12′ (1 eq, 50 mg) were dissolved in DMF (1 mL) then stirred with DIPEA (2 eq, 52 mu) for 10 min at rt. The reaction was then cooled with an ice bath to 0C and COMU (1 eq, 64 mg) was added. The mixture was stirred at 0C for lh then the bath was removed and the reaction was allowed to reach rt and continued for 5h. The compound was extracted using EtOAc three times (5 mL x 3). The combined organic layers were then washed several times with saturated NaHC03 until washing solution was colourless. The resulting organic solution was dried, filtered and evaporated. The product was then purified using column chromatography on silica gel DCM/MeOH (90/10) (Rf = 0.2) as a pale yellow solid (65 mg, 65%). 1H NMR (600 MHz, CDC13) Mix of rotamers ratio (1/1) delta 7.69 (d, J = 7.9 Hz, 2H), 7.62 (d, J = 7.9 Hz, 1H), 7.56 (d, J = 6.7 Hz, 1H), 7.46 (m, 2H), 7.37-7.26 (m, 4H), 6.96 (t, J = 7.4 Hz, 1H), 6.89 (t, J = 7.4 Hz, 1H), 4.95 (s, 1H), 4.69 (m, 3H), 4.50 (s, 1H), 4.40 (s, 1H), 3.64 (m, 1H), 3.30 (m, 1H), 2.88 (m, 1H), 2.81 (t, J = 6.7 Hz, 1H), 2.76 (t, J = 6.7 Hz, 4H), 2.59 (t, J = 7.1Hz, 2H), 2.51 (q, J = 7.0 Hz, 2H), 2.11 (quint, J = 7.4 Hz, 1H), 2.05 (quint, J = 7.4 Hz, 1H), 1.10 (t, J = 7.1Hz, 3H), 0.98 (t, J = 7.1Hz, 3H). 13C-NMR (CDC13, 150 MHz) Mix of rotamers delta: 167.5, 166.5, 162.2 (d, JCF = 240 Hz), 161.4, 161.3, 156.8, 156.5, 144.1, 143.6, 139.8, 139.3, 136.8, 135.4, 131.5 (d, JCF = 3 Hz), 131.2 (d, JCF = 9 Hz), 131.1 (d, JCF = 3 Hz), 129.8 (m), 128.8, 128.0 (m), 127.7 (m), 127.4, 127.3, 127.2, 125.9 (m), 124.4 (m), 121.3, 121.2, 115.7 (d, JCF = 23 Hz), 115.6 (d, JCF = 23 Hz), 51.4, 50.4, 50.3, 50.1, 49.2, 47.8, 47.3, 46.1, 36.6, 36.5, 32.1, 32.0, 28.5, 28.4, 20.9, 20.8, 11.8;

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, 356058-42-9, 2-(2-((4-Fluorobenzyl)thio)-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetic acid.

Reference:
Patent; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE); UNIVERSITE DE LA REUNION; MEILHAC, Olivier; JESTIN, Emmanuelle; GUIBBAL, Florian; BENARD, Sebastien; (80 pag.)WO2019/63634; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 20781-06-0, 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 20781-06-0, name is 2,4-Diaminopyrimidine-5-carboxaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

1mmol 2,4-diamino-5-pyrimidinecarbaldehyde with1.1mmol benzoyl hydrazide is dissolved in 25ml ethanol solvent,Add 0.15 mmol of trifluoroacetic acid,Heat and stir the reaction for 6-8h,TLC monitors the progress of the reaction,Add 50ml of water after the reaction is completed.Stirring solids precipitated,Filtering,Drying gave a yellow solid.Yield 79%, m.p. 250-252 C;

According to the analysis of related databases, 20781-06-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Central China Normal University; He Hongwu; Zhou Yuan; (70 pag.)CN109503496; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 1558-17-4, name is 4,6-Dimethylpyrimidine. A new synthetic method of this compound is introduced below., Safety of 4,6-Dimethylpyrimidine

Dimethyl pyrimidine-4,6-dicalpharboxylalphate (llalpha)To a heated solution (75C) of 4,6-dimethylpyrimidine (846 mg, 8.00 mmol) and NaOH (211 mg, 5.28 mmol) in water (3 mL) was added a solution OfKMnO4 (5.28 g in 25 mL water) overl5 min. The resulting mixture was stirred at 80C for 3 hrs. The hot solution was filtered hot and manganese dioxide washed with hot water (8 mL). The filtrate and washings were concentrated to 5 mL and acidified with cone. HCl to pH 2-3. After cooling, the precipitation was collected, yielding 591 mg of crude pyridine-4,6-dicarboxylic acid. The diacid was then dissolved in MeOH (15 mL) and cone. H2SO4 (1.5 mL) was added dropwise carefully. The mixture was refluxed for 24 hrs, cooled to room temperature and concentrated in vacuo. The resultant oily residue was neutralised with sat. NaHCO3 and extracted with EtOAc (3 x 30 mL). The combined organic extracts were washed with H2O (50 mL) and brine (5OmL), dried over Na2SO4, filtered and concentrated. The product was then purified by column chromatography (petroleum ether 40-60 : EtOAc 5 : 5 to 3 :7) yielding 311 mg (20%) of 11 a 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, 1558-17-4, 4,6-Dimethylpyrimidine.

Reference:
Patent; ISIS INNOVATION LIMITED; SCHOFIELD, Christopher, Joseph; MCDONOUGH, Michael; ROSE, Nathan; THALHAMMER, Armin; WO2010/43866; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 633328-98-0, 5-Chloro-1H-pyrazolo[4,3-d]pyrimidine, 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, Recommanded Product: 5-Chloro-1H-pyrazolo[4,3-d]pyrimidine, blongs to pyrimidines compound. Recommanded Product: 5-Chloro-1H-pyrazolo[4,3-d]pyrimidine

In a 50 mL round-bottom flask with a stir bar, 5-chloro-1H-pyrazolo[4,3-d]pyrimidine (Oxchem, 600 mg, 3.88 mmol) and triethylamine (649 mul, 4.66 mmol) were dissolved in CH2Cl2 (12.9 mL). Di-tert-butyl dicarbonate (991 mul, 4.27 mmol) was added, and the reaction mixture was stirred at r.t. for 1 h. The reaction mixture was then diluted with water, extracted with CH2Cl2, and the combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by Biotage Isolera (860 mg, 87%). LCMS calculated for C10H12ClN4O2 (M+H)+ m/z=255.1; found 255.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,633328-98-0, 5-Chloro-1H-pyrazolo[4,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Vechorkin, Oleg; Liu, Kai; Pan, Jun; Sokolsky, Alexander; Ye, Hai Fen; Ye, Qinda; Yao, Wenqing; Hummel, Joshua; (117 pag.)US2018/72741; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1546-78-7, 4-Hydroxy-6-(trifluoromethyl)pyrimidine, 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, 1546-78-7, blongs to pyrimidines compound. name: 4-Hydroxy-6-(trifluoromethyl)pyrimidine

A solution of 6-(trifluoromethyl)pyrimidin-4-ol (5.0 g, 30.5 mmol), phosphoryl chloride (3.41 mL, 36.6 mmol), and quinoline (2.16 mL, 18.3 mmol) in toluene (50 mL) was stirred at 100 C. for 5 h. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (10% EtOAc/Hexane) to yield the desired product (1.20 g, 21.6%). 1H NMR (400 MHz, CDCl3): 9.21 ppm (1H, s), 7.78 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1546-78-7, its application will become more common.

Reference:
Patent; Xue, Chu-Biao; Zheng, Changsheng; Feng, Hao; Xia, Michael; Glenn, Joseph; Cao, Ganfeng.; Metcalf, Brian W.; US2006/4018; (2006); 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. 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4316-97-6

Example 1(Z)-ter -Butyl 4-((6-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-5- methy Ipyrimidin-4-yl)oxy)piperidine- 1 -carboxylate.Step I: Preparation of tert- uty 4-((6-chloro-5-methylpyrimidin-4-yl)oxy)piperidine- l – carboxylate.Pottasium tert-butoxide (3.4 gm, 0.0306 moles) was added to a solution of tert- butyl 4-hydroxypiperidine-l -carboxylate (6.8 gm, 0.0368 moles) and 4, 6-dichloro-5- methylpyrimidine (5.0 gm, 0.0368 moles) in dry THF at 0 C and the reaction mixture was stirred for 15-20 hours at 30 C. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic extract was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure to collect 5.1 gm off- white solid product.’HNMR: Patent; CADILA HEALTHCARE LIMITED; PINGALI, Harikishore; ZAWARE, Pandurang; WO2012/46249; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 187035-79-6, name is Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate, the common compound, a new synthetic route is introduced below. Recommanded Product: 187035-79-6

To a solution of l-isopropyl-7-(methylsulfonyl)-l,2,3,4- tetrahydrobenzo[4,5]imidazo[l,2-a]pyrazine (5.0 mg, 0.02 mmol, prepared according to example 1) in DMSO (1 mL) was added ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5- carboxylate (8.7 mg, 0.03 mmol), DIEA (6.6 mg, 0.05 mmol) under N2. The mixture was stirred at 100 C for 2 h. The mixture was diluted with water (5 mL) and extracted with EtOAc (3 x5 mL). The combined organic layers were washed with brine (5 mL), dried over anhydrous Na2S04, filtered, concentrated and then purified by preparative TLC to afford a racemic mixture of ethyl 2-(l-isopropyl-7-(methylsulfonyl)-3,4- dihydrobenzo[4,5]imidazo[l,2-a]pyrazin-2(lH)-yl)-4-(trifluoromethyl)pyrimidine-5- carboxylate (5.6 mg, 64% yield) as a white solid. LC- m/z 512.2 [M+H]+. 1H NMR (CDC13 400MHz): delta 8.98 (s, 1H), 8.07-7.98 (m, 1H), 7.93-7.83 (m, 2H), 6.16 (d, J = 6.4 Hz, 1H), 5.53-5.41 (m, 1H), 4.43-4.32 (m, 3H), 4.28-4.16 (m, 1H), 3.92-3.79 (m, 1H), 3.09 (s, 3H), 2.61-2.46 (m, 1H), 1.40 (s, 3H), 1.38-1.32 (m, 3H), 1.08 (d, J = 6.8 Hz, 3H).

The synthetic route of 187035-79-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; DONG, Chengguo; FAN, Yi; LEFTHERIS, Katerina; LOTESTA, Stephen; SINGH, Suresh, B.; TICE, Colin; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2013/138568; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 99586-66-0, 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, 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, Recommanded Product: 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, blongs to pyrimidines compound. Recommanded Product: 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile

The procedure mentioned in Scheme 6 was used with (S)-methyl 6-((2-(1- ((tert-butoxycarbonyl)amino)propyl)-4-oxo-3 -phenyl-3 ,4-dihydroquinazolin-5- yl)amino)hexanoate 1.3b (110.0 mg, 0.21 mmol) and trifluoroacetic acid (480.0 mg, 4.21 mmol, 0.32 ml) in dichioromethane (2.1 ml). The resulting mixture was stirred at room temperature for 3 hours and worked-up (Method A) to form (S)-methyl 6-((2-(1- aminopropyl)-4-oxo-3 -phenyl-3 ,4-dihydroquinazolin-5-yl)amino)hexanoate 6.11. This free amine 6.11 was used with 2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile (53.0 mg, 0.32 mmol) and diisopropylethylaime (81.0 mg, 0.63 mmol, 110.0 pi) in n-butanol (0.5 ml) and heated at 130 C for 2 hours. The remaining residue was purified by flash chromatography on silica gel using 0-100% EtOAc/Hexanes to afford the product methyl (5)- 6-((2-(1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)propyl)-4-oxo-3-phenyl-3,4- dihydroquinazolin-5-yl)amino)hexanoate 6.2q (97.0 mg, 0.174 mmol) in 83% yield. LC-MS (method 1): tR = 3.25 mi mlz (M + H)+ = 555.3.

The synthetic route of 99586-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; GREWAL, Gurmit; THAKUR, Ashish; TAWA, Gregory James; FERRER, Marc; SIMEONOV, Anton M.; (191 pag.)WO2018/237007; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3680-69-1, 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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

To a suspension of commercial 4-chloro-7H-pyrrolo[2,3-d]pyrimidine 10.75 g (70.00 mmol) in 150mL DCM, and added 1-bromopyrrolidine-2,5-dione (18.69 g, 105.00 mmol) at ambient temperature overnight. Upon the reaction completion, large amounts of precipitates formed. The precipitates were collected by filtration, and the filtrate was removed under reduced pressure to get the solid, washed with DCM, to yield of the title compound as yellow solid (15.00 g, 92% yield). 1H NMR (400 MHz, DMSO) delta 12.97(s, 1H), 8.63 (s, 1H), 7.95 (d, J 2.6 Hz, 1H).

Statistics shows that 3680-69-1 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Zhang, Chufeng; Pei, Heying; He, Jun; Zhu, Jiali; Li, Weimin; Niu, Ting; Xiang, Mingli; Chen, Lijuan; European Journal of Medicinal Chemistry; vol. 169; (2019); p. 121 – 143;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia