Pyrimidines

Electric Literature of 955368-90-8, 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. 955368-90-8, name is 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one. A new synthetic method of this compound is introduced below.

Cuprous iodide (42.82 mg, 224.85 mumol), N,N’-dimethyllethylenediamine (22.20 mg, 251.83 mumol, 27.07 muL) and potassium carbonate (42.88 mg, 310.29 mumol) were added separately into the compound I1 (49.98 mg, 224.85 mumol) and 72-1 (56.00 mg, 224.85 mumol) in dioxane (3 mL) solution, the reaction mixture was stirred at 95C for 1 hour under nitrogen atmosphere, then concentrated and added 20 mL ammonia, extracted by EA 150 mL (50 mLx3) and washed by saturated brine 30 mL, dried over anhydrous sodium sulfate, then filtered to give the crude compound. The crude product was purified by silica gel column chromatography (PE/EA=3/1) 72-1. MS m/z: 391.0 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,955368-90-8, 2-Allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Shijiazhuang Sagacity New Drug Development Co., Ltd.; QIAN, Wenyuan; YANG, Chundao; LI, Zhengwei; LI, Jie; LI, Jian; CHEN, Shuhui; (137 pag.)EP3572413; (2019); A1;,
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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. 4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine, molecular formula is C4HCl2N3O2, 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: C4HCl2N3O2

To a 500 ml three neck round bottomed flask, 4,6-dichloro-5-nitropyrimidine (25 g, 129 mmole) was dissolved in CH2Cl2 (300 ml) and cooled to 0 C. To this, dibenzylamine (49.6 ml, 257.7 mmole) was added dropwise by maintaining temperature at 0 C. and stirred for 1.5 h at same temperature. The reaction mixture was diluted with CH2Cl2 and washed with water. The combined organic layer was dried over sodium sulphate and concentrated to give the crude product which was purified by trituration with n-pentane to yield 38 g of N,N-dibenzyl-6-chloro-5-nitropyrimidin-4-amine (83.06% yield).

With the rapid development of chemical substances, we look forward to future research findings about 4316-93-2.

Reference:
Patent; Principia Biopharma Inc.; Owens, Timothy D.; US2014/142099; (2014); A1;,
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Pyrimidine – Wikipedia

Related Products of 183438-24-6 ,Some common heterocyclic compound, 183438-24-6, molecular formula is C4H2BrIN2, 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.

Example 29A 3-[(5-bromopyrimidin-2-yl)oxy]quinuclidine 3-Hydroxy quinuclidine (Aldrich, 254 mg, 2 mmol) in tetrahydrofuran (10 ml) was treated with potassium tert-butoxide (Aldrich, 224 mg, 2 mmol) at ambient temperature for 1 hour. The mixture was treated with 2-iodo-5-bromo-pyrimidine (TCl, 568 mg, 2 mmol), stirred at room temperature for 1 hour, treated with water (5 mL), and extracted with chloroform:isopropyl alcohol (10:1) (3*20 mL). The extracts were combined and concentrated. The title compound was purified by chromatography (SiO2, CH2Cl2: MeOH: NH3H2O, 90:10:2, Rf. 0.20) as oil (210 mg, yield, 71%). 1H NMR (MeOH-d4, 300 MHz) delta 1.56-1.68 (m, 1H), 1.70-1.90 (m, 2H), 2.05-2.30 (m, 2H), 2.79-3.06 (m, 5H), 3.40-3.48 (m, 1H), 5.11 (m, 1H), 8.64 (s, 2H) ppm. MS (DCl/NH3) m/z 284 (M+H)+, 286 (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,183438-24-6, its application will become more common.

Reference:
Patent; Abbott Laboratories; US2005/137226; (2005); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 871254-61-4, Adding some certain compound to certain chemical reactions, such as: 871254-61-4, name is 2,4-Dichloropyrimidine-5-carbaldehyde,molecular formula is C5H2Cl2N2O, 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 871254-61-4.

To a flask containing MeOH (24.0 mL), was added 2,4- dichloropyrimidine-5-carbaldehyde (1.5159 g, 1.0 equiv.), PPTS (215.0 mg, 0.1 equiv.) and trimethyl orthoformate (6.0 mL). The reaction mixture was stirred at 65 C for 14 h, cooled to rt and concentrated. The resulting residue was purified via column chromatography to yield the title compound as an oil (1.4361 g, 75% yield). NMR (400 MHz, Chloroform-^ d 8.73 (s, 1H), 5.54 (s, 1H), 3.38 (s, 7H). LC-MS: m/z 223, 225 [M+H]+.

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. 871254-61-4, 2,4-Dichloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; KONTEATIS, Zenon D.; LI, Mingzong; LIU, Peng; MEDEIROS, Matthew; REZNIK, Samuel K.; SUI, Zhihua; TRAVINS, Jeremy M.; POPOVICI-MULLER, Janeta; ZHOU, Shubao; MA, Guangning; (298 pag.)WO2019/191470; (2019); A1;,
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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. 4359-87-9, name is 2,4,6-Trichloro-5-nitropyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 4359-87-9

PREPARATION 112 2-Chloro-6-morpholin-4-yl-9-(tetrahydro-2W-pyran-4-yl)-7,9-dihydro-8H-purin-8- o a) 4-(2,6-Dichloro-5-nitropyrimidin-4-yl)morpholine A solution of morpholine (362 mg, 4.16 mmol) and triethylamine (0.58 mL, 4.16 mmol) in methylene chloride (11 mL) was added dropwise to a cooled (0 C) solution of 2,4,6- trichloro-5-nitropyrimidine (950 mg, 4.16 mmol) in methylene chloride (25 mL) and the resulting mixture was stirred overnight at ambient temperature. Solvent was then evaporated and the crude was purified by flash cromatography (3:1 hexanes/ethyl acetate) to yield the title compound (780 mg, 67%) as a yellow solid. LRMS (m/z): 279 (M+1)+ 1H NMR (300 MHz, CDCI3) delta ppm 3.77 (m, 4H), 3.50 – 3.67 (m, 4H).

The synthetic route of 4359-87-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi; WO2011/157397; (2011); A1;,
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Synthetic Route of 374930-88-8, 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. 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, 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.

A mixture of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (684 mg, 2.0 mmol), 4-fluorophenol (1.1 g, 5.0 mmol), copper (650 mg, 10.0 mmol) and Cs2CO3 (6.5 g, 20.0 mmol) in pyridine (15 mL) was heated at 120 C. for 12 h. The mixture was cooled to RT, diluted with ethyl acetate (200 mL) and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=20/1) to afford the title compound (200 mg, 27%) as a brown solid. MS (ES+) C19H23FN4O3 requires: 374. found: 319 [M-56+1]+.

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 374930-88-8, tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate.

Reference:
Patent; Hodous, Brian L.; Kim, Joseph L.; Wilson, Kevin J.; Wilson, Douglas; Zhang, Yulian; US2015/111887; (2015); A1;,
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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. 3029-64-9, name is 2,4,6-Trichloro-5-cyanopyrimidine, the common compound, a new synthetic route is introduced below. Quality Control of 2,4,6-Trichloro-5-cyanopyrimidine

9.00 g (35 mmol) of 10-phenylphenol azine was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent under ice bath conditions.Stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h.2.07 g (10 mmol) of 2,4,6-trichloro-5-cyanopyrimidine was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 4.87 g of a white solid powder was obtained in a yield of 55.8percent.

The synthetic route of 3029-64-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Gao Wenzheng; Huang Xinxin; Ren Xueyan; (27 pag.)CN109553606; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 17321-97-0, 2-Amino-4-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, 17321-97-0, blongs to pyrimidines compound. COA of Formula: C6H6N4

General procedure: To the solution of corresponding quinazolone intermediate 13a(13b, 13c or 13d) in DCM (4 mL/1 mmol substrate)was added TFA (1mL/1 mmol substrate) dropwise at 0 C, and the resultant mixturewas stirred at room temperature. After 13a (13b, 13c or 13d) wastotally consumed, saturated NaHCO3 solution was added dropwiseat 0 C to adjust the PH value to 7. Following extraction with DCM,the organic layer was washed with brine, dried over anhydrousNa2SO4, and concentrated in vacuo to afford the Boc-deprotectedsecondary amine as slightly yellow solid.The mixture of corresponding Boc-deprotected secondaryamine (1.0 eq), 6-chloro-9H-purine (1.5 eq), DIPEA (4.0 eq) and t-BuOH (15 mL/1 mmol secondary amine) was stirred at 80 C underN2 atmosphere. After the secondary aminewas totally consumed, t-BuOH was removed in vacuo, and the residue was dissolved inDCM. The solution was washed with saturated NaHCO3 solution,dried over anhydrous Na2SO4, and concentrated in vacuo. Finally,the crude product underwent flash column chromatography (DCM/EA 5:1-1:1, V/V) to afford the purine derivative (14 or 15e17) aspale solid. Compounds with 4-aminopyrimidine-5-carbonitrile, 2-amino-6-methylpyrimidine-5-carbonitrile, 2-fluoro-9H-purine or2-chloro-9H-purine as HBs were prepared via similar procedure tothat for 14e17. However, the eluents utilized in the final flash columnchromatography of 21, 22, 24, 25 and 27 were different (DCM/EA 15:1-5:1, V/V, for 21, 24 and 27; DCM/EA 20:1-8:1, V/V, for22 and 25). The NMR spectra of 14e17, 28 and 29 indicated theexistence of rotamers.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17321-97-0, its application will become more common.

Reference:
Article; Chen, Yuqing; Fang, Fang; Gui, Shuangying; Hu, Yongzhou; Li, Jiaming; Liang, Jingtai; Liang, Xiao; Ma, Xiaodong; Meng, Chang; Tao, Qiangqiang; Wang, Huchuan; European Journal of Medicinal Chemistry; vol. 191; (2020);,
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Pyrimidine – Wikipedia

Synthetic Route of 18592-13-7, 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.18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione, molecular formula is C5H5ClN2O2, molecular weight is 160.5584, as common compound, the synthetic route is as follows.

A mixture of 132 (0.170 g; 0.35 mmol), chloromethyluracil (0.061 g; 0.38 mmol), NaI (0.057 g; 0.38 mmol) and [K2CO3] (0.053 g; 0.38 mmol) in dimethylacetamide (8 [ML)] was heated at [80C] under argon atmosphere for 17 hours. The crude mixture was evaporated and purified by flash chromatography eluting with a gradient 2-8% of 3.5 N NH3 in MeOH/methylene chloride to give after trituration in ether/heptane Example 47 as a pale brown solid. Yield: 41% MS-ESI: 615 [[M+H] +] [‘H] NMR [(CDC13)] : 1.20-1. 40 (br m, 4H); 1.56 (br m, [4H)] ; 1.63 (s, 6H); 2.36 (s, 6H); 2.50 (br m, 8H); 3.29 (s, 2H); 3.58 (s, 2H); 4.15 (br m, 1H); 4.75 (br m, 1H); 5.53 (s, 1H) ; 6.80 (s, 1H) ; 6.96 (s, 1H) ; 7.21 (s, 2H); 7.97 (br s, 1H) ; 8.25 (s, 1H); 8.53 (br s, 1H).

The chemical industry reduces the impact on the environment during synthesis 18592-13-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/18480; (2004); A1;,
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Pyrimidine – Wikipedia

Related Products of 2915-16-4, Adding some certain compound to certain chemical reactions, such as: 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine,molecular formula is C16H11ClN2, 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 2915-16-4.

Shenzhen’s gre-syn chemical technology (http://www.gre-syn.com/) in a nitrogen environment, 2-chloro-4,6-diphenylpyrimidine (20 g, 75.0 mmol) was dissolved in tetrahydrofuran (THF) 0.3 L , here it was stirred into the compound I-7 (38.1 g, 75.0 mmol) and tetrakis (triphenylphosphine) palladium (0.87 g, 0.75 mmol). Into the potassuim carbonate (25.9 g, 188 mmol) in saturated water it was heated to reflux at 80 for 15 hours. After the reaction was completed, the reaction solution into water and extracted with dichloromethane (DCM) and then water was removed with anhydrous MgSO4, filter and was concentrated under reduced pressure. The obtained residue was purified by flash column chromatography to give the Compound 9 (43.2 g, 94%).

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. 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHEIL INDUSTRIES INC.; HAN ILL, LEE; SU JIN, HAN; YOUNG KWON, KIM; EUN SUN, YU; HO KUK, JUNG; (66 pag.)KR2015/117173; (2015); A;,
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