Pyrimidines

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.866648-53-5, name is 6-Chloro-N,N-dimethyl-2-(trifluoromethyl)pyrimidin-4-amine, molecular formula is C7H7ClF3N3, molecular weight is 225.6, as common compound, the synthetic route is as follows.name: 6-Chloro-N,N-dimethyl-2-(trifluoromethyl)pyrimidin-4-amine

General procedure: 4-hydroxy was prepared in Reference Example 60 3- (piperidin-4-yl) -4- (trifluoromethyl) -1,4,5,7- tetrahydro -6H- pyrazolo [3,4-b] pyridin-6-one hydrochloride (100 mg, 0.293 mmol) in dimethyl sulfoxide (0.5 mL) solution of, N, N- diisopropylethylamine (59.8muL, 0.352mmol) and 3-chloro-6- (trifluoro methyl) pyridazine (80.2mg, 0.439mmol) was added, and the mixture was stirred overnight at room temperature.The reaction mixture was diluted with ethyl acetate, washed successively with water, saturated aqueous solution of ammonium chloride and brine, dried over anhydrous sodium sulfate, under reduced pressure, and the solvent was evaporated.The obtained residue was purified by silica gel column chromatography to obtain [eluent: ethyl acetate / methanol = 100 / 0-90 / 10 (gradient) to give the title compound (30% 39.8 mg, yield) It was.Instead of 3-chloro-6- (trifluoromethyl) pyridazine, using 6-chloro -N, N-dimethyl-2- (trifluoromethyl) pyrimidin-4-amine (150mg, 0.665mmol), carried the reaction was carried out in the same manner 80 C. manner to that described in example 43, the title compound (91 mg, yield: 28%) was obtained

At the same time, in my other blogs, there are other synthetic methods of this type of compound,866648-53-5, 6-Chloro-N,N-dimethyl-2-(trifluoromethyl)pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo company limited; Sato, Rie; Kobayashi, Katsuhiro; Kaneko, Toshio; (188 pag.)JP2015/113323; (2015); 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. 4595-61-3, name is Pyrimidine-5-carboxylic acid, molecular formula is C5H4N2O2, 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 4595-61-3

1,1?-carbonyldiimidazole (1.23 g, 7.57 mmol) was added to a suspension of pyrimidine-5-carboxylic acid (783 mg, 6.31 mmol) in DCM (20 mL) and the mixture was stirred at room temperature for 15 min before addition of N,O-dimethylhydroxylamine hydrochloride (739 mg, 7.57 mmol). The mixture was stirred at room temperature for 5 d, then was diluted with saturated aqueous NH4Cl and water and extracted with DCM. The organic phase was washed with water, and the aqueous phases were back-extracted with DCM. The organic phase was dried (Na2SO4), filtered, and concentrated, affording the crude title compound as a light yellow oil which was used without further purification in the next reaction

With the rapid development of chemical substances, we look forward to future research findings about 4595-61-3.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22536-61-4, 2-Chloro-5-methylpyrimidine, 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, name: 2-Chloro-5-methylpyrimidine, blongs to pyrimidines compound. name: 2-Chloro-5-methylpyrimidine

5-Methyl-2-vinylpyrimidine, Example 28.1 A 3 L 3-necked round bottomed flask was fitted with a reflux condenser, a temperature controller and a septum and was charged with 2-chloro-5-methylpyrimidine (81 mL, 778 mmol), potassium vinyltrifluoroborate (156 g, 1167 mmol), triphenylphosphine (18.02 mL, 78 mmol), cesium carbonate (156 mL, 1945 mmol) and a large stir bar. Water (1565 mL) was added, and the mixture was stirred for several min and then THF (244 mL) was added. Argon was bubbled through the mixture for 5 min and then palladium (II) chloride (1.72 g, 38.9 mmol) was added. The reaction was further sparged with argon for 5 mins. The temperature was raised to 62 C. and stirring continued to completion. The reaction was then cooled to RT and filtered through two Whatman GF/F filter cups, rinsing with ether. The mixture was transferred to a separatory funnel, and the layers were separated. The aqueous layer was further extracted with diethyl ether (4*200 mL). The organic layers were combined and dried over anhydrous MgSO4 and then filtered. The mixture was partially concentrated on a rotary evaporator at 20 C. and 115 torr for an extended period of time to give an orange liquid. The material was further purified by Kugel Rohr distillation to isolate the title compound (65.4 g, 70%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) delta 2.31 (s, 3H), 5.68 (d, J=10.56 Hz, 1H), 6.55 (d, J=17.22 Hz, 1H), 6.86 (dd, J=17.41, 10.56 Hz, 1H), 8.54 (s, 2H). LCMS-ESI (pos) m/z:121.1 (M+H)+.

The synthetic route of 22536-61-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEDLEY, Simon J.; HOUZE, Jonathan; JUDD, Ted C.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YEH, Wen-Chen; (415 pag.)US2017/320860; (2017); A1;,
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Pyrimidine – Wikipedia

Related Products of 63200-54-4, Adding some certain compound to certain chemical reactions, such as: 63200-54-4, name is 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine,molecular formula is C6H3Cl2N3, 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 63200-54-4.

To a solution of 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (6.6 g, 35.3 mmol) in ethanol (200 mL) was added sodium hydrogen carbonate (2.96 g) and Palladium on carbon (10%, 0.66 g). The mixture was stirred under an atmosphere of hydrogen at room temperature for 3 h. The mixture was filtered then filtrate absorbed onto silica gel. Flash chromatography, eluting with chloroform/methanol 4/1, afforded 2-chloro-5H- pyrrolo[3,2-d]pyrimidine (3.3 g, 61%). Also recovered from the column was 5H- pyrrolo[3,2-d]pyrimidine (1.5 g)

According to the analysis of related databases, 63200-54-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2009/62258; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde, 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, 14160-93-1, blongs to pyrimidines compound. Computed Properties of C5H4ClN3O

4-benzyloxy-3-chloro-phenylamine Compound 1c (8.9 g, 38 mmol) was added to a solution of Compound 1b (6.0 g, 38 mmol) and Et3N (10.6 mL, 76 mmol) in DMSO (38 mL, 1M). The mixture was warmed at 100 C. for 3 hrs. The reaction mixture was cooled, then diluted with H2O and extracted with EtOAc (3¡Á). The organic extract was washed with H2O (4¡Á), concentrated onto SiO2 (30 g) and purified via column chromatography (Horizon, 65+, 60 to 100% EtOAc/hexanes) to afford 4-amino-6-(4-benzyloxy-3-chloro-phenylamino)-pyrimidine-5-carbaldehyde Compound 14 (8.29 g, 61%) as a yellow solid. H E NMR (400 Mhz, CD3OD, warm) delta 10.15 (s, 1H), 8.05 (s, 1H), 7.77 (d, J=2.4 Hz, 1H), 7.48 (d, J=76 Hz, 2H), 7.38 (m, 4H), 7.11 (d, J=8.8 Hz, 1H), 5.18, (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14160-93-1, its application will become more common.

Reference:
Patent; Connolly, Peter J.; Hughes, Terry V.; Wetter, Steven K.; US2009/111810; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 504-17-6, 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. 504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, 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.

General procedure: A mixture of aldehyde (1 mmol), malanonitrile (1 mmol), barbituricor thiobarbituric acid (1 mmol), and DES (0.1 g, 36 mol%)was stirred in refluxing water (2 mL) for an appropriate period oftime. The reaction progress was followed by TLC (eluent: EtOAc: nhexane).After completion of the reaction, the mixture was dilutedwith water (4 mL) and filtered off. Finally, the solid product wasrecrystallized from warm ethanol if necessary.

According to the analysis of related databases, 504-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Biglari, Mohammad; Shirini, Farhad; Mahmoodi, Nosrat O.; Zabihzadeh, Mehdi; Mashhadinezhad, Maryam; Journal of Molecular Structure; vol. 1205; (2020);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 130049-82-0, 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 130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one. This compound has unique chemical properties. The synthetic route is as follows.

Example-5 Purification of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H- pyrido[1,2-a]pyrimidin-4-one using organic acid13.6 gm of oxalic acid dihydrate was taken in 250 ml water. 25 gm of 3-(2-chloroethyl)-9- hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one was added and stirred at about 35-4O0C for about 30 minutes. Clear solution was obtained. The solution was treated with charcoal and filtered. The filtered solution of oxalate salt was treated with ~25 gm of potassium acetate up to pH 4.8.The obtained mass was stirred at 0-50C for about 1 hour. The obtained solid mass was washed with cold water. The wet mass was stirred with water for about 1 hour at 25-300C. The mass was filtered and dried to give purified 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H- pyrido[1 ,2-a]pyrimidin-4-one. Wt. =15.2 gm

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 130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one.

Reference:
Patent; CADILA PHARMACEUTICALS LTD.; MODI, Indravadan, Ambalal; SODAGAR, Keval, Rameshchandra; VINEET, Malik; JAIN, Sudhir, Hukamchand; PARIKH, Sanjay, Natvarlal; SHARMA, Arun, Omprakash; BAPAT, Uday, Rajaram; KHAMAR, Bakulesh, Mafatlal; WO2010/64134; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 22536-61-4, 2-Chloro-5-methylpyrimidine, 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, Application In Synthesis of 2-Chloro-5-methylpyrimidine, blongs to pyrimidines compound. Application In Synthesis of 2-Chloro-5-methylpyrimidine

(E)-2-(but-2-en-2-yl)-5-methylpyrimidine, Example 10.01. 2- Chloro-5-methyl-pyrimidine (18 mL, 151 mmol), potassium (Z)-but-2-en-2- yltrifluoroborate (Sigma Aldrich, 31 g, 191 mmol), tricyclohexylphosphine (8.5 g, 30.2 mmol), and Pd2(dba)3 (13.82 g, 15.09 mmol) were added to a flask, which was then degassed and backfilled with nitrogen. To the flask was added 1,4-dioxane (252 mL) and aqueous potassium phosphate tribasic (37.5 mL, 453 mmol). The resulting reaction was heated at 100 C for 16 h. The reaction was then cooled to RT. The residue was filtered through a plug of silica gel, then loaded onto silica gel (0-20% EtOAc in heptanes) to afford (E)-2-(but-2-en-2-yl)-5-methylpyrimidine 10.01 (19 g, 125 mmol, 83% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-61-4, 2-Chloro-5-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 633328-95-7 , The common heterocyclic compound, 633328-95-7, name is 5-Bromo-2-chloro-4-methylpyrimidine, molecular formula is C5H4BrClN2, 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.

5-Bromo-2-isopropoxy-4-methylpyrimidine (B10.1) (0382) To a solution of 5-bromo-2-chloro-4-methylpyrimidine (3.0 g, 14.5 mmol) in THF (30 mL) was added NaH (1.74 g, 44 mmol), it was stirred at rt for 0.5 h. Then propan-2-ol (2.6 g, 44 mmol) was added, the mixture was stirred at rt for 3 h. The mixture was concentrated, the residue was diluted with water (20 mL), extracted with EA (20¡Á3 mL). The organic layer was dried and concentrated, the crude product was purified by flash chromatography (silica gel; EA_PE=1:4) to give the title compound (2.8 g, 83%)) as a gray solid. LC-MS: [M+H]+=231.0; 232.9.

The synthetic route of 633328-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; CHAN, Ho Man; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (134 pag.)US2016/176882; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 29274-24-6, 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 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-(ethoxycarbonyl)phenylboronic acid (6.08 g, 31.37 mmol), K3P04 (11 g, 52.28 mmol), Pd(PPh3)4 (0.4 g) and 5-chloropyrazolo[l,5-a]pyrimidine (4 g, 26.14 mmol) in a mixture of 1,4-dioxane (250 mL) and H20 (50 mL) was stirred at room temperature. The reaction mixture was refluxed overnight under argon and the reaction mixture was diluted with EtOAc and washed in turn with water and brine. The organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to give the crude product which was purified by flash column chromatography (silica gel, eluent petroleum ether/EtOAc 50:50) to afford ethyl 4-(pyrazolo[l,5-a]pyrimidin-5-yl)benzoate (3.6 g, 52%, LC-MS 95%) as a yellow solid.

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 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; CHENNAMANENI, Lohitha Rao; WO2015/50505; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia