Pyrimidines

Application of 18740-39-1 ,Some common heterocyclic compound, 18740-39-1, molecular formula is C6H2Cl2N2S, 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: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 °C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 percent yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

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. 18740-39-1, 2,4-Dichlorothieno[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
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Application of 1421433-87-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1421433-87-5 as follows.

D25 7-chloro-1-isopropyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one A mixture of 7-chloro-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one (700 mg, 4.08 mol), 2-iodopropane (1.04 g, 6.12 mmol) and Cs2CO3 (2.66 g, 8.16 mmol) in acetonitrile (15 mL) was refluxed for 3 h, filtered and concentrated to remove solvent to get crude product (700 mg) without further purification. LC-MS (ESI): m/z 214 [M+H]+; 0.93 min (ret time)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1421433-87-5, its application will become more common.

Reference:
Patent; Glaxo Group Limited; Wan, Zehong; Long, Kai; Sang, Yingxia; Su, Xiaobo; US2014/179715; (2014); A1;,
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Reference of 113583-35-0, 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.113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine, molecular formula is C7H10N2O4S, molecular weight is 218.23, as common compound, the synthetic route is as follows.

The resulting intermediate n-propyl 4-(2-hydroxy-benzylamino) benzamide (22.7 g, 0.08 mol), 17.44 g (0.08 mol) of 2-methylsulfonyl-4,6-dimethoxypyrimidine are dissolved into 500 ml dioxane. 22 g (0.16 mol) of potassium carbonate is added at room temperature. The mixture is warm to reflux temperature for 11 hours, then suction filtered. The filter cake is washed with dioxane (50 ml*2) and the mother liquor is concentrated and recrystallized from ethyl acetate, giving 25.4 g of white solid product n-propyl 4-[2-(4,6-dimethoxy-2-pyrimidinyloxy)-benzylamino]-benzamide (I-78). The yield is 75%. m.p.: 96-97 C.; m/z: 423 (M+); 1H-NMR (CDCl3, delta): 7.14-7.88 (m, 8H), 6.51 (d, 1H), 5.78 (s, 1H), 4.45 (s, 2H), 4.19 (t, 2H), 3.80 (s, 6H), 1.77 (m, 2H), 1.03 (t, 3H) ppm

The chemical industry reduces the impact on the environment during synthesis 113583-35-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Lue, Long; Chen, Jie; Wu, Jun; Ling, Wen; Mao, Lisheng; Li, Mingzhi; Cai, Xian; Peng, Weili; Wu, Yong; Wu, Shenggan; Wang, Hongjun; Wang, Guochao; Cui, Hu; Han, Shidong; Qiu, Weilian; Wang, Yonghua; US2003/220198; (2003); A1;,
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Electric Literature of 51940-63-7 ,Some common heterocyclic compound, 51940-63-7, molecular formula is C7H7ClN2O2, 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.

ethyl 6-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylate 700 mg (2.85 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 470 muL (2.73 mmol) DIPEA were added to 500 mg (2.68 mmol) ethyl 6-chloropyrimidine-4-carboxylate in 10 mL DMF and the reaction mixture was stirred for 1 h at RT. The reaction mixture was diluted with water and stirred for 30 min. The precipitate was suction filtered, washed with water and dried at 50 C. in the CAD. Yield: 620 mg (59% of theoretical) ESI-MS: m/z=396 (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,51940-63-7, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
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Reference of 186046-78-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 186046-78-6 as follows.

Example 55 1-(Benzothiazole-2-sulfonyl)-4-{[4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-piperazin-2-one The title compound was synthesised by the reaction of 1-(benlzothiazole-2-sulfonyl)-piperazin-2-one trifluoroacetic acid salt with [4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetic acid as per the procedure of Example 52. 1H NMR (500 MHz; DMSO-d6) delta 11.00 (brs, 1H), 8.34 (m, 1H), 8.26 (m, 1H), 7.90 (d, 0.6H), 7.84 (d, 0.4H), 7.72 (m, 2H), 7.44 (d, 4H), 7.37 (t, 4H), 7.29 (t, 2H), 6.94 (t, 1H), 6.79 (s, 1H), 4.82 (s, 1.2H), 4.72 (s, 0.8H), 4.45 (s, 0.8H), 4.28 (s, 1.2H), 4.22 (t, 1.2H), 4.07 (t, 0.8H), 3.99 (t, 1.2H), 3.86 (t, 0.8H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,186046-78-6, its application will become more common.

Reference:
Patent; Kim, Sung Kee; Lee, Hyunil; Lim, Jong Chan; Choi, Hoon; Jeon, Jae Hoon; Ahn, Sang Youl; Lee, Sung Hee; Yoon, Won Jun; US2003/225252; (2003); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 332133-92-3, 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. 332133-92-3, name is 4-(Tributylstannyl)pyrimidine. A new synthetic method of this compound is introduced below.

A mixture of 3~(2-amino-5~(bis(4-mefhoxybenzyl)amino)-8~bromo~ il,2,4]triazolo[l,5-c]pyrimidin-7-yl)benzonitrile (350 mg, 0.61 mmol), 4- (tributylstannyi)pyrimidine (210 pL, 0.67 mmol), ietrakis(triphenylphosphine)pailadium(0) (70 mg, 0.060 mmol), copper(l) iodide (23 mg, 0.12 mmol) and cesium fluoride (180 mg, 1.2 mmol) in dioxane (4.7 mL) was heated and stirred at 140 C for 30 min in a microwave reactor. The reaction mixture was then cooled to r.t, filtered through a Celite plug (washed with DCM), and concentrated. The resulting material was purified by silica gel column chromatography eluting with 0-20% MeOH/DCM to give the desired product. LC-MS calculated for C32H28N9O2 (M+H)+: m/z = 570.2; found 570 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,332133-92-3, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; WANG, Xiaozhao; GAN, Pei; HAN, Heeoon; HUANG, Taisheng; MCCAMMANT, Matthew S.; QI, Chao; QIAN, Ding-Quan; WU, Liangxing; YAO, Wenqing; YU, Zhiyong; ZHANG, Fenglei; (284 pag.)WO2019/168847; (2019); A1;,
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Synthetic Route of 39906-04-2, 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. 39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine, molecular formula is C5H5Cl2N3, 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 microwave vial was charged with 3′-aminoacetanilide 29 (300 mg, 2.0 mmol), 5-amino-4,6-dichloropyrimidine (10) (328 mg, 2.0 mmol), acetic acid (100 muL) and isobutanol (10 mL) and was irradiated at 150 C for 30 min. After cooling, dichloromethane was added (20 mL) and the crude reaction mixture was washed with saturated aqueous NaHCO3 (20 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by flash chromatography (dichloromethane:methanol).Yield: 300 mg (54%).

According to the analysis of related databases, 39906-04-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Aguado, Leire; Canela, Maria-Dolores; Thibaut, Hendrik Jan; Priego, Eva-Maria; Camarasa, Maria-Jose; Leyssen, Pieter; Neyts, Johan; Perez-Perez, Maria-Jesus; European Journal of Medicinal Chemistry; vol. 49; (2012); p. 279 – 288;,
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Electric Literature of 2972-52-3, 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. 2972-52-3, name is 2,4-Dichloro-5-pyrimidinecarbonyl chloride, molecular formula is C5HCl3N2O, 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.

Ethyl 2,8,9J0J7J9.22-heptaazatricvclori6.3.1. .l0ltricosa-l(2U (23 8 8(22I19- entaene-21 -carboxylate (1279) (1280) A solution of 2,4-dicMoropyrirnidine-5-carbonyl chloride (1.00 g, 4.76 mmol) in ethanol (6.0 mL) was added DIPEA (2.5 mL, 14.4 mmol) slowly at 0 C under nitrogen. After 30 min, hex-5-yn-l -amine (0.476 g, 4.91 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 3.5 h, then was added drop wise to a solution of 6-azidohexan-l -amine (0.801 g, 5.64 mmol) in ethanol (4.0 mL) at 50 C. After the reaction was complete (monitored by LCMS), the mixture was diluted with water (10 mL) and concentrated under a reduced pressure and filtered. The yellow solid was washed with water and dried under vacuum to be used in the next step without further purification (0.723 g, 39% over 3 steps).

According to the analysis of related databases, 2972-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; ZHANG, Weihe; FRYE, Stephen; WO2015/157127; (2015); A1;,
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Application of 776-53-4 ,Some common heterocyclic compound, 776-53-4, molecular formula is C8H11N3O2S, 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 12 (4-Amino-2-methanesulfanyl-pyrimidin-5-yl)-methanol A solution of 4-amino-2-methanesulfanyl-pyrimidine-5-carboxylic acid ethyl ester (13.36 g, 63 mmol) in 250 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (3.82 g, 100 mmol) in 250 mL of tetrahydrofuran. After 30 minutes, the reaction was cooled to 0 C., and isopropyl alcohol was added until bubbling diminished. The reaction was quenched with 15 mL of water, 15 mL of 15% NaOH, and 50 mL of water, and the mixture was stirred for 1 hour. The white precipitate was removed by filtration, washing with ethyl acetate. The filtrate was concentrated in vacuo and 3:1 hexane:ethyl acetate was added. The solids were collected, washed with 3:1 hexane:ethyl acetate, followed by hexane. The solid was dissolved in ethyl acetate, and the solution was dried over magnesium sulfate. Filtration followed by concentration in vacuo gave 8.14 g (76%) of (4-amino-2-methanesulfanyl-pyrimidin-5-yl)-methanol. Analysis calculated for C6H9N3OS: C, 42.09; H, 5.30; N, 24.54. Found: C, 42.31; H, 5.24; N, 24.27.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,776-53-4, its application will become more common.

Reference:
Patent; Booth, Richard John; Chatterjee, Arindam; Malone, Thomas Charles; US2004/224958; (2004); A1;,
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Related Products of 720-01-4, 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 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate (1 g, 3.93mmol) and N,N-diisopropylethylamine (1.37mL, 7.87mmol) in 2-propanol (8 mL) was added morpholine (0.42 mL, 4.92 mmol). The mixture was stirred at room temperature for 3 h and was then concentrated in vacuo. The resulting residue was purified by column chromatography (40% EA/Hex) to give ethyl 2-(trifluoromethyl)-4-moropholinopyrimidine-5-carboxylate as a white solid (1.2g, 98%).1H NMR (DMSO-d6, 400MHz): 8.71(1H, s), 4.32(2H, q), 3.68(4H, t), 3.59(4H, t), 1.31(3H, t). ESI-MS: 306 (M+1)

According to the analysis of related databases, 720-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Purushothaman, Baskaran; Arumugam, Parthasarathy; Kulsi, Goutam; Song, Joon Myong; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 673 – 690;,
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