Day: September 10, 2021

Reference of 4359-87-9 ,Some common heterocyclic compound, 4359-87-9, molecular formula is C4Cl3N3O2, 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 suspension of 2,4,6-trichloro-5-nitropyrimidine (0.8g, 3.5mmol) inTHF (30ml) was added [l-(4-Amino-phenyl)-cyclobutyl]-carbamic acid tert-butyl ester (0.827g, 3.15mmol) at 15C. The mixture was stirred for 30min at 15C. The reaction mixture was concentrated and was purified by flushing chromatography on silica gel (eluting with Hexane EtOAc=100/l~3/l) to give tert-butyl l-(4-(2,6-dichloro-5-nitropyrimidin-4- ylamino)phenyl)cyclobutylcarbamateas a yellow solid (0.45g, 31.5% yield). ‘HNMR (CDCI3, 400 MHz): S9AS(s, 1H), 7.49 (s, 4H), 5.12 (s, ??,), 2.55-2.51(m, 4?), 2.13-2.04(m, 1H),1.89-I.86(m, lH),1.42(s, 9H); LC/MS: (ESI+) e/z: 454.3 [M+l]+, 456.3 [M+3]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4359-87-9, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5751-20-2, 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.5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one, molecular formula is C5H6N2OS, molecular weight is 142.18, as common compound, the synthetic route is as follows.

Example 11 Synthetic route

The chemical industry reduces the impact on the environment during synthesis 5751-20-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Changyou; ZOU, Wuxin; HUA, Yuxia; DANG, Qun; WO2011/133444; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-61-4, Adding some certain compound to certain chemical reactions, such as: 22536-61-4, name is 2-Chloro-5-methylpyrimidine,molecular formula is C5H5ClN2, 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 22536-61-4.

2-Chloro-5-methyl-pyrimidine (18 mL, 151 mmol), potassium (Z)-but-2-en-2- yltrifluoroborate (Sigma Aldrich, 31 g, 191 mmol), tricyclohexyiphosphine (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 100C for 16 h. The reaction was then cooled to RT. The residue was filtered through a plug of silica gel and then loaded onto silica gel (0-20% EtOAc in heptanes) to afford (E)-2-(but-2-en-2-yl)-5-methylpyrimidine, Example 371.01 (19 g, 125 mmol), in 83% yield.

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. 22536-61-4, 2-Chloro-5-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3435-28-7, 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. 3435-28-7, name is 6-Methylpyrimidin-4-amine, molecular formula is C5H7N3, 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) 2-Chloro-N-(6-methyl-pyrimidin-4-yl)-acetamide 6-Methyl-pyrimidin-4-yl amine (545 mg) was suspended in DCE (5 mL) and chloroacetylchloride (0.4 mL) was added dropwise. The reaction was heated in a microwave at 80 C. for 5 mins. The reaction mixture was cooled, filtered and a solid obtained.

According to the analysis of related databases, 3435-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bull, Richard James; Skidmore, Elizabeth Anne; Ford, Rhonan Lee; Mather, Andrew Nigel; Mete, Antonio; US2011/172237; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia