Tag: M.W:200-300

Reference of 353272-15-8, 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. 353272-15-8, name is 6-Chloro-5-iodopyrimidin-4-amine, molecular formula is C4H3ClIN3, 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.

To a mixture of (5 -2-(l-amiiioethyl)-5-chloro-3-cyclopropylquinazolin-4(3H)- one (50 mg, 0.189 mmoi ), 6-chloro-5-iodopyrimidin-4-amine (48 mg, 0.189 mmoi) and DIPEA (49 mg, 0.379 mmoi) in n-BuOH (1 mL) was heated to reflux and stirred further for 16 hours, then cooled to rt, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v) = 100/1 ) to give the title compound as a yellowish solid (49 mg, yield 53%). MS (ESI, pos. ion) m/z: 483.0 [M+H]+; FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, CDC13) delta (ppm): 7.98 (s, 1H), 7.55-7.53 (m, 2H), 7.43-7.41(dd, J = 3.6, 5.6 Hz, 1H), 6.41-6.39 (d, J= 7.8 Hz, 1H), 6.12-6.05 (m, 1H), 5.04 (s, 2H), 3.05-3.03 (m, 1H), 1.59- 1.57 (d, J= 6.2 Hz, 3H), 1.43-1.41 (m, 2H), 1.14-1.10 (m, 1H), 0.95-0.86 (m,lH).

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 353272-15-8, 6-Chloro-5-iodopyrimidin-4-amine.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WANG, Liang; WANG, Tingjin; WU, Weibin; (123 pag.)WO2015/175579; (2015); A1;,
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Synthetic Route of 187035-79-6, 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. 187035-79-6, name is Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

The intermediate 8-(((tert-butyldiphenylsilyl)oxy)methyl)- 1 -isopropyl-7- (methylsulfonyl)- l,2,3,4-tetrahydropyrazino[l,2-a]indole was prepared following a procedure analogous to that described in Preparation 4. The mixture of compound 8-(((tert- butyldiphenylsilyl)oxy)methyl)- l-isopropyl-7-(methylsulfonyl)-l, 2,3,4- tetrahydropyrazino[l,2-a] indole (0.19 mmol), ethyl 2-chloro-4-(trifluoromethyl)pyrimidine- 5-carboxylate (97 mg, 0.38 mmol) and DIEA (100 mu,, 0.57 mmol) in j-PrOH / CH2C12 (1 mL / 0.5 mL) was stirred at 50C for 8 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with EtOAc/hexanes (1/1) to give racemic ethyl 2-(8-(hydroxymethyl)- l-isopropyl-7-(methylsulfonyl)-3,4- dihydropyrazino[ 1 ,2-a]indol-2( lH)-yl)-4-(trifluoromethyl)pyrimidine-5-carboxylate. LC- MS m/z 563 [M+Na]+. 1H NMR (400 MHz, CD3OD): delta 9.31 (s, 1H), 8.11 (s, 1H), 7.80 (s, 1H), 6.55 (s, 1H), 6.02 – 5.92 (m, 1H), 5.23 – 5.17 (m, 1H), 5.07 (s, 2H), 4.52 – 4.47 (m, 1H), 4.34 (q, J = 7.2 Hz, 2H), 4.19 – 4.06 (m, 1H), 4.00 – 3.93 (m, 1H), 3.27 (s, 3H), 2.42 – 2.32 (m, 1H), 1.36 (t, J = 7.2 Hz, 3H), 1.18 (d, J = 6.8 Hz, 3H), 1.03 (d, J = 6.8 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,187035-79-6, Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; DONG, Chengguo; FAN, Yi; LEFTHERIS, Katerina; LOTESTA, Stephen; SINGH, Suresh, B.; TICE, Colin; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2013/138568; (2013); A1;,
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Synthetic Route of 1224944-77-7, 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. 1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate. A new synthetic method of this compound is introduced below.

A mixture of ethyl 5-chloropyrazolo[1 ,5-a]pyrimidine-3-carboxylate (677 mg, 3.00 mmol), methanamine (3.0 ml, 2.0 M, 6.0 mmol) and N,N-diisopropylethylamine (1.6 ml, 9.0 mmol) in 2-propanol (20 ml) was refluxed for 5 h. Upon cooling, ice water was added and the mixturewas extracted with ethyl acetate (3x). The combined organic phases were filtrated through a silicone filter and concentrated to give the title compound (570 mg).[C-MS (Method 1): R = 0.74 mm; MS (ESIneg): m/z = 219 [M-H]1H-NMR (400 MHz, DMSO-d6) 6 [ppm]: 1.258 (7.44), 1.276 (16.00), 1.293 (7.62), 1.296 (2.96), 1.338 (1.13), 2.902 (6.89), 2.914 (6.83), 4.155 (3.10), 4.173 (9.99), 4.191 (9.82),4.209 (2.93), 6.336 (1.70), 6.355 (1.74), 7.855 (1.41), 7.867 (1.40), 8.126 (5.66), 8.482 (1.60), 8.501 (1.56).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1224944-77-7, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); 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. 13544-44-0, name is 2,4-Dichloro-5-iodopyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 13544-44-0

The mixture of 2,4-dichloro-5-iodopyrimidine (400 mg) and N-(3-aminopropyl)carbamic acid tert-butyl ester (0.24 ml) in 3 ml of ACN with 0.23 ml od TEA was stirred overnight at rt. The product was then precipitated by the addition of water and collected and dried as an opaque yellow oil. 20 mg of this product was then reacted with N-(3-aminophenyl)pyrrolidine-1-carboxamide (14.9 mg, prepared previously28) overnight at 115C in 1 ml of MeOH in a sealed vial with 1.5 mul concn HCl. Then 1 ml of TFA was added overnight at rt to deprotect. The product was then purified by RP HPLC to give the final product, which was then lyophilized to give a white powder. Overall yield of 16%.

The synthetic route of 13544-44-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lazarus, Michael B.; Shokat, Kevan M.; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5483 – 5488;,
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Electric Literature of 1207518-63-5 ,Some common heterocyclic compound, 1207518-63-5, molecular formula is C8H6ClN3O2, 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 5 Step 2: 4-Chloro-7-[(2R,3R,4R,5R)-3-ethynyl-3-hydroxy-4-(4-methyl- benzoyloxy)-5-(4-methyl-benzoyloxymethyl)-tetrahydro-furan-2-yl]-7H-pyrrolo[2,3- d]pyrimidine-5-carboxylic acid methyl ester; A dry flask is charged with 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid methyl ester (698 mg, 3.3 mmol, 1.1 equiv.), NaH (156 mg as 60% dispersion in oil, 3.9 mmol) and acetonitrile (10 ml), stirring for 10 mins. Then crude compound 1 ,2-anhydro-2-C-ethynyl-3,5- bis(4-methylbenzoyl)-alpha-D-ribofuranose (1.2 g, 3.0 mmol) in acetonitrile (5 ml) is added and the reaction is heated at 80 0C for 3 h. The mixture is neutralized to pH = 7.0 by addition of 1 N HCI solution and evaporated under vacuum. Ethyl acetate (80 ml) is added and the mixture is washed with 1 N HCI solution (20 ml), H2O (20 ml), brine (20 ml), dried (Na2SO4), filtered, concentrated and purified by flash column to give 4-chloro-7-[(2R,3R,4R,5R)-3-ethynyl-3- hydroxy-4-(4-methyl-benzoyloxy)-5-(4-methyl-benzoyloxymethyl)-tetrahydro-furan-2-yl]-7H- pyrrolo[2,3-d]pyrimidine-5-carboxylic acid methyl ester. ESI-MS (pos.): 604.3 [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,1207518-63-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; CHEN, Yen Liang; DURAISWAMY, Jeyaraj; HALLER, Sarah; KEIM, Matthias; KONDREDDI, Ravinder Reddy; YIN, Zheng; WO2010/15643; (2010); A1;,
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Synthetic Route of 1374639-77-6 ,Some common heterocyclic compound, 1374639-77-6, molecular formula is C12H14ClN3O, 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.

A solution of compound(4) (4 g, 15.9 mmol) in THF (60 mL) was stirred at 10-15 Cunder nitrogen atmosphere, manganese(IV)oxide (2.8 g, 31.7mmol) was added to the mixture and stirring was continuedfor 2 hours at 29 C. Progress of the reaction was monitoredby TLC. After completion of the reaction, the resultingmixture was filtered through celite bed and concentratedunder vacuum. The crude product was purified by columnchromatography using 2% of ethyl acetate and hexane aseluent to obtain compound (5). White crystalline solid,Yield: 72%, 152-154 C. 1H NMR (400 MHz, DMSO-d6):1.65-1.68 (m, 2H, -CH2), 1.99-2.03 (m, 4H, CH2), 2.14-2.16(m, 2H, CH2), 5.60-5.68 (m, 1H, -NH-CH-), 7.72 (s, 1H, Ar-H), 9.92 (s, 1H, Ar-H), 9.98 (s, 1H, CHO). 13C NMR (75.46MHz, DMSO-d6): 184.6, 156.6, 153.5, 137.5, 130.1, 116.9,56.3, 31.03, 24.9. ESI-HRMS (m/z): Calcd. ForC12H12ClN3O:249.6969. Found: m/z 249.0971 [M+].

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. 1374639-77-6, (2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Singaram, Kulathooran; Marimuthu, Dhamodaran; Baskaran, Selvakumar; Chinaga, Suresh K.; Shanmugarajan, Dhivya; Vadivel, Thangavel; Combinatorial Chemistry and High Throughput Screening; vol. 20; 8; (2017); p. 703 – 712;,
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Pyrimidine – Wikipedia

Synthetic Route of 148550-51-0, 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. 148550-51-0, name is Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, molecular formula is C8H10N2O4S, 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: 60percent Sodium hydride (w/w) in mineral oil (0.0015 mol) was added to a mixture of appropriate III (0.001 mol) in THF (15 ml) under the condition of inert atmosphere using N2 flow at 5°C. The reaction mixture was kept for 1 h at room temperature. A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.0015 mol) in THF (15 ml) was slowly added to reaction mixture. The resulting reaction mixture was stirred for 2-3 h at 5°C. The distilled water (20 ml) was added. The reaction mixture was extracted (10 ml x 3) with dichloromethane. The separated organic layer was dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure to obtain crude product, recrytallized by ethyl acetate.

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 148550-51-0, Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate.

Reference:
Article; Rajak, Harish; Agarawal, Avantika; Parmar, Poonam; Thakur, Bhupendra Singh; Veerasamy, Ravichandran; Sharma, Prabodh Chander; Kharya, Murli Dhar; Bioorganic and Medicinal Chemistry Letters; vol. 21; 19; (2011); p. 5735 – 5738;,
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Pyrimidine – Wikipedia

Reference of 138274-14-3, 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. 138274-14-3, name is 5-(Benzyloxy)-2-chloropyrimidine, molecular formula is C11H9ClN2O, 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.

To a 100 mL two-necked vial, 5-benzyloxy-2-chloropyrimidine 34b (0.50 g, 2.3 mmol), thiophene-3-boronic acid(0.44 g, 3.4 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (0.17 g, 0.23 mmol).After the addition, the reaction system was replaced three times with nitrogen. Toluene (20 mL), ethanol (10 mL) and aqueous sodium carbonate (5.2 mL, 10 mmol, 2 mol/L) were added under nitrogen. The reaction solution was then warmed to 80 C for 2 hours.The heating was stopped, and after the reaction solution was cooled to room temperature, the diatomaceous earth was suction filtered, and the filtrate was washed with water (10 mL) and saturated sodium chloride solution (10 mL).Dry over anhydrous sodium sulfate, concentrate by suction filtration, and the residue obtained was purified by silica gel column chromatography[Petroleum ether / ethyl acetate (v / v) = 10/1] purified,The title compound 42a (0.50 g, yield 82%)

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 138274-14-3, 5-(Benzyloxy)-2-chloropyrimidine.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Gu Zheng; Li Jianhao; Li Zheng; Wang Weihua; Tan Haoxiong; Wang Xuli; Cui Yunzeng; Xie Zeqiang; Zhang Yingjun; (101 pag.)CN109251166; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1211443-61-6, 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 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a suspension of 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (5) (586 mg, 2 mmol) in 20 mL 1,4-dioxane were added compound 3a-f, 3i-u(2 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), BINAP (62 mg, 0.1 mmol) and Cs2CO3 (978 mg, 3 mmol) and the flask was purged with Ar. Then the flask was sealed and the mixture was heated for 12 h at 100. The reaction was cooled to rt, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4a-f, 4i-o, 4r-u.

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 1211443-61-6, 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide.

Reference:
Article; Li, Yongtao; Guo, Qingxiang; Zhang, Chao; Huang, Zhi; Wang, Tianqi; Wang, Xin; Wang, Xiang; Xu, Guangwei; Liu, Yanhua; Yang, Shengyong; Fan, Yan; Xiang, Rong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3231 – 3237;,
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Synthetic Route of 56844-12-3, 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 56844-12-3, name is 6-Bromo-4-chlorothieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 6-Bromo-4-chlorothieno[2,3-d]pyrimidine(5a) (200 mg, 0.802 mmol) was mixed with 1-phenylethanol (2a) (118 mg, 0.962 mmol), Cs2CO3( 313 mg, 0.962 mmol) and acetonitrile (2 mL). The reaction was then stirredunder nitrogen atmosphere at reflux and followed by GC. The mixture was cooledto rt, diluted with EtOAc (40 mL), washed with sat. aq. KHCO3 (20mL), water (2×20 mL) and brine (30 mL). The combined organic fractions weredried over Na2SO4 and concentrated in vacuum. Crudeproduct was absorbed onto Celite 545 and purified by silica gel columnchromatography (n-pentane/EtOAc,6/1). This gave 245 mg (0.730 mmol, 91%) of 6a as an off-white 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 56844-12-3, 6-Bromo-4-chlorothieno[2,3-d]pyrimidine.

Reference:
Article; Han, Jin; Sundby, Eirik; Hoff, Bage H.; Journal of Fluorine Chemistry; vol. 153; (2013); p. 82 – 88;,
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