Pyrimidines

Application of 10132-07-7, 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 10132-07-7, name is 4-Amino-2,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

N-tert-Butoxycarbonylpiperidinyl-4-methylamine (5.0 g) was slowly added to a stirred solution of 2,4-dichloro-6-aminopyrimidine (5.7 g) in 1-pentanol (20 mL). The solution was stirred at 120 C. for 12 hours. The solution was then concentrated and the resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/9) to give Intermediate 224-I (3.6 g) in a 45% yield. Intermediate 224-I (2.4 g) was then dissolved in CH2Cl2 (80 mL) and 20% TFA/CH2Cl2 (20 mL) was added. The solution was stirred at room temperature overnight. The solution was then concentrated and the resultant residue was purified by column chromatography on silica gel (21% NH3 (aq)/MeOH=1/19) to afford Intermediate 224-II (1.5 g) in a 90% yield. Intermediate 222-III (3.3 g) prepared in Example 222 was added to a solution of Intermediate 224-II (1.9 g) in MeOH (40 mL). The mixture was stirred at 60 C. for 12 hours. NaBH4 (0.3 g) was then added at 0 C. After the mixture was stirred for 1 hour, an aqueous solution of NH4Cl (10%, 10 mL) was added. The mixture was extracted with EtOAc, dried over anhydrous MgSO4, and filtered. The solution thus obtained was then concentrated. The resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/1) to afford Intermediate 224-III (1.5 g) in a 40% yield. N1-Morpholine-N1-piperazine ethane (370 mg) was added to Intermediate 224-III (300 mg) in 1-pentanol (1 mL). The mixture was stirred at 120 C. for 12 hours. After the solution was concentrated, the residue was treated with water and extracted with CH2Cl2. The organic layer was separated and concentrated. The resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/9) to afford Intermediate 224-IV (281 mg) in a 70% yield. A solution of 20% TFA/CH2Cl2 (3 mL) was added to a solution of Intermediate 224-IV (281 mg) in CH2Cl2 (2 mL). The reaction mixture was stirred for 8 hours at room temperature and concentrated by removing the solvent. The resultant residue was purified by column chromatography on silica gel (21% NH3 (aq)/MeOH=1/19) to afford Compound 224 (200 mg) in a 85% yield. Compound 224 was then treated with 1 M HCl (4 mL) in CH2Cl2 (2 mL) for 0.5 hours. After the solvents were removed, the residue was treated with ether and filtered to give hydrochloride salt of Compound 224. CI-MS (M++1): 544.4.

According to the analysis of related databases, 10132-07-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yen, Chi-Feng; Hu, Cheng-Kung; Chou, Ming-Chen; Tseng, Chen-Tso; Wu, Chien-Huang; Huang, Ying-Huey; Chen, Shu-Jen; King, Chi-Hsin Richard; US2006/281712; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
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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 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine

The 4,4 ‘ – (6-chloro-pyrimidine -2,4-diyl) two morpholine (301 mg, 1 . 06mmol), 7-bromo-8 – (trifluoromethyl) – 3,4-dihydro -2H-pyrido [3,2-b] [1,4] oxazine (200 mg, 0 . 71mmol),were taken and then duplex pinacone borate (350 mg, 1 . 38mmol), cesium fluoride (500 mg, 3 . 3mmol), palladium acetate (20 mg, 0 . 09mmol) and butyl b (1-adamantyl) diphenylphosphinobiphenyl (64 mg, 0 . 18mmol), were sequentially added to the toluene and methanol (4 ml, 1:1) in the mixed solvent, and added to the above mentioned solution, under nitrogen protection,at 70 C oil bath for 1 hour. After the reaction, concentrating, separating TLC (petroleum ether: ethyl acetate = 1:2), to obtain the title compound (45 mg, yield 14%).

With the rapid development of chemical substances, we look forward to future research findings about 10244-24-3.

Reference:
Patent; Shandong Xuan Bamboo Pharmaceutical Technology Co., Ltd.; Wu, Yong qian; (49 pag.)CN105461714; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 57489-77-7, 5,7-Dichloropyrazolo[1,5-a]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, Computed Properties of C6H3Cl2N3, blongs to pyrimidines compound. Computed Properties of C6H3Cl2N3

Example 3; [A General Procedure for the Synthesis of a Pyrazolo[1,5-a]pyrimidine Derivative Represented by General Formula (V-04)]; A mixture was prepared by adding N-chlorosuccinamide, N-bromosuccinamide or iodine monochloride (0.011 mol) to a chloroform (50 mL) solution containing 5,7-dichloropyrazolo[1,5-a]pyrimidine (V-03) (0.01 mol) at room temperature. The mixture was stirred under heating and reflux until all solid was dissolved and the starting materials disappeared by TLC. The mixture was poured into ice/water to separate the organic layer, which was washed with aqueous Na2CO3 solution, subsequently dried with MgSO4, and the solvent was removed under vacuum. The residue was purified by silica gel chromatography to obtain 3-halo-5,7-dichloropyrazolol,5-alpyrimidine (V-04). The typical yield of the reaction ranged from 60 to 90%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57489-77-7, 5,7-Dichloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; TEIJIN PHARMA LIMITED; US2006/135514; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4318-56-3, 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. 4318-56-3, name is 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C5H5ClN2O2, 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.

3-Methyl-6-chloro uracil (12 g, 76 mmol),Compound 3 (17.2 g, 80 mmol) and K2CO3 (10 g,80 mmol) in DMSO (100 mL) was stirred for 2 h and the reaction was diluted with water and extracted with EtOAc. The organic phase was dried over MgSO4 and the solvent was removed. Purification by column chromatography gave 4,13.2 g (60% yield).

According to the analysis of related databases, 4318-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Institute of Pharmaceutical Industry; China Pharmaceutical Industry Research Institute; Chen, Wu; Liu, Xiangkui; Ji, Zhongde; Zhu, Xueyan; Yuan, Zhedong; (10 pag.)CN105418580; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.3001-72-7, name is 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine, molecular formula is C7H12N2, molecular weight is 124.1836, as common compound, the synthetic route is as follows.Safety of 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine

General procedure: The p-nitrophenyl carbonate derivative (0.3 g) was dissolved in AR grade THF (5 mL) at room temperature and DBU or DBN (2 equiv) was added. The temperature of the reaction mixture was raised to 60 C and stirring was continued for 1 h. After completion, the reaction mixture was extracted with ethyl acetate (2 × 30 mL), the organic layer washed with saturated NaHCO3 solution, water, brine and dried over anhydrous Na2SO4. Thesolvent was evaporated and the crude compound was purified by column chromatography

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3001-72-7, 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Vangala, Madhuri; Shinde, Ganesh P.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2086 – 2092;,
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Pyrimidine – Wikipedia

Related Products of 153435-63-3, 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.153435-63-3, name is 2-(Tributylstannyl)pyrimidine, molecular formula is C16H30N2Sn, molecular weight is 369.1328, as common compound, the synthetic route is as follows.

3-(6,7-Dimethoxy-quinolin-4-yloxy)-quinolin-2-ol (50 mg), diphosphorus pentaoxide (51 mg), and tetrabutylammonium bromide (69 mg) were suspended in 1,2-dichlorobenzene (1 ml), and the suspension was stirred at 140C for 1.5 hr. The reaction mixture was cooled to room temperature, and a 10% aqueous sodium hydrogencarbonate solution was added thereto. The mixture was extracted with chloroform, and the chloroform layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a chloroform-methanol system to give 4-(2-bromo-quinolin-3-yloxy)-6,7-dimethoxy-quinoline (5 mg, yield 8%). 4-(2-Bromo-quinolin-3-yloxy)-6,7-dimethoxy-quinoline (50 mg), tetrakistriphenylphosphine palladium (0) (28 mg), and copper(II) oxide (19 mg) were suspended in N,N-dimethylformamide (1.5 ml). 2-Tributylstannylpyrimidine (90 mg) was added to the suspension, and the mixture was stirred at 100C overnight. The reaction mixture was cooled to room temperature and was then filtered. The solvent was removed from the filtrate by distillation under the reduced pressure. Water was added thereto, and the mixture was extracted with dichloromethane. The dichloromethane layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with a chloroform-methanol system to give the title compound (28 mg, yield 56%). 1H-NMP, (CDCl3, 400 MHz): delta 4.05 (s, 6H), 6.44 (d, J = 5.2 Hz, 1H), 7.43 – 7.78 (m, 8H), 7.88 (s, 1H), 8.11 (d, J = 8.4 Hz, 1H), 8.52 (d, J = 5.2 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 411 (M++1)

Statistics shows that 153435-63-3 is playing an increasingly important role. we look forward to future research findings about 2-(Tributylstannyl)pyrimidine.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5177-27-5, 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. 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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 2,4-dichloropyrimidin-5-amine (0.5 g, 3.04 mmol), sodium methoxide (0.66 g, 12.19 mmol) and methanol (10 ml) was refluxed for 16 hours. The solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 2-chloro-4-methoxypyrimidin-5-amine after flash chromatography (100-200 mesh size silica gel, 20-25% ethyl acetate in hexane) was 0.35 g. N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of 2-chloro-4-methoxypyrimidin-5-amine (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.

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 5177-27-5, 5-Amino-2,4-dichloropyrimidine.

Reference:
Patent; MEDEIA THERAPEUTICS LTD; RATILAINEN, Jari; GOLDSTEINS, Gundars; WO2014/191632; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 29274-24-6 ,Some common heterocyclic compound, 29274-24-6, molecular formula is C6H4ClN3, 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.

General Procedure 32-Methyl-4-pyrazolo[1 ,5-a]pyrimidin-5-yl-but-3-yn-2-ol (5a); [00151] Compound 1a, 2-methyl-but-3-yn-2-ol (1.5 equivalents), Pd CI2[PPh3]2 (5 mol %) and CuI (10 mol %) in diethyl amine is refluxed under argon for 2 h (TLC control), then cooled and evaporated to dryness. The residue is dissolved in dichloromethane; the target product is isolated by column chromatography (silica gel, ethyl acetate – hexane, 1 :2). The solvent is evaporated under reduced pressure; the residue is crystallized from diethyl ether to give the title compound in good yield.1H NMR (DMSO-d6, 400 MHz) delta (ppm), 1.51 (s, 6H), 6.69 (s, 1 H), 6.98 (d, 1 H), 8.22 (s.1 H)1 9.06 (d, 1 H). m/z (APCI+) 202 (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,29274-24-6, its application will become more common.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGaA; HENRICH, Markus; WEIL, Tanja; NAGEL, Jens; GRAVIUS, Andreas; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; FOTINS, Juris; WO2010/63487; (2010); A1;,
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Pyrimidine – Wikipedia

Reference of 3921-01-5, 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. 3921-01-5, name is 2,4-Dibromopyrimidine, molecular formula is C4H2Br2N2, 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: Starting material2,4-dibromopyrimidine (CAS Registry Number: 3921-01-5) (24.46 g, 102.82 mmol)Was dissolved in THF (360ml) in a round bottom flask, 4,4,5,5-tetramethyl-2- (naphthalen-1-yl-ethyl) -1,3,2-dioxaborolane (CAS Registry Number: 1280709-91-2) (29.54 g, 113.11 mmol),Pd (PPh3) 4 (4.75 g, 4.11 mmol),K2CO3 (42.63 g, 308.47 mmol),Water (180 ml)And the mixture was stirred at 90 C.After the reaction was completed, the reaction mixture was extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 18.03 g (yield: 60%) of the product.

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 3921-01-5, 2,4-Dibromopyrimidine.

Reference:
Patent; Duksan Neolux Co.,Ltd.; Park Mu-jin; Choi Yeon-hui; Moon Seong-yun; Jeong Ho-yeong; Song Hyeon-ju; Lee Mun-jae; Kwon Jae-taek; (46 pag.)KR2017/103105; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3435-28-7 ,Some common heterocyclic compound, 3435-28-7, molecular formula is C5H7N3, 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.

To a solution of Example 154a (100 mg, 0.26 mmol,) and Example 154b (45 mg, 0.39 mmol) in DMA (2.5 mL) were added Pd2(dba)3 (24 mg, 0.026 mmol), Xantphos (30 mg, 0.052 mmol) and Cs2CO3 (340 mg, 1.04 mmol). The mixture was degassed by nitrogen for 3 times and stirred at 130oC for 2 h. When completed, the reaction was cooled to r.t., diluted with MeOH (5 mL) and filtered. The filtrate was purified directly by Prep-HPLC to give the desired product Example 154 (40.0 mg, 34.2% yield) as a white solid. LCMS [M+1] + = 457.2.1H NMR (400 MHz, DMSO-d6) d 11.03 (s, 1H), 10.27 (s, 1H), 9.14 (s, 1H), 8.55 (s, 2H), 7.78 (s, 1H), 7.65-7.57 (m,3H), 7.30 (d, J = 7.9 Hz, 1H), 3.93 (s, 3H), 3.69 (s, 3H), 2.97 (s, 1H), 2.34 (s, 3H), 1.07 (s, 2H), 1.01 (s 2H).

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. 3435-28-7, 6-Methylpyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; KALDOR, Stephen W.; (0 pag.)WO2020/86616; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia