Tag: M.W:200-300

Electric Literature of 10457-14-4, 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.10457-14-4, name is 2,4-Bis((trimethylsilyl)oxy)pyrimidine, molecular formula is C10H20N2O2Si2, molecular weight is 256.449, as common compound, the synthetic route is as follows.

To a solution of Compound 39 (927 mg, 2.00 mmol) in dry CH2CI2 (5 mL) was added HBr (1.16 mL, 4.28 mmol, 33% in AcOH) under N2. And the resultant mixture was stirred under N2 for 17 h. The reaction mixture was washed with twice H2O and NaHCC>3, dried (MgSC^) and concentrated under reduced pressure to give the crude bromide (838 mg) as a pale yellow oil. In a separate flask, uracil (269 mg, 2.40 mmol) and (NH4)2S04 (16 mg) in hexamethyldisilazane (5.0 mL) was heated to reflux under N2 for 22 h. The reaction mixture was concentrated under reduced pressure and dried under high vacuum to give the crude bis-TMS-uracil as a colorless oil. The crude bromide in dry CHCI3 (10 mL) was added to crude bis-TMS-uracil via cannula under N2. The resultant mixture was heated to reflux under N2 for 18 h and then quenched with H2O and stirred at RT for 30 min. The phases were separated and the aqueous phase was extracted twice with CH2CI2. The combined organic extracts were dried (MgS04) and concentrated under reduced pressure. Recrystalhzation from EtOH gave Compound 40 (598 mg) as a colorless solid.

Statistics shows that 10457-14-4 is playing an increasingly important role. we look forward to future research findings about 2,4-Bis((trimethylsilyl)oxy)pyrimidine.

Reference:
Patent; NOVADEX PHARMACEUTICALS AB; ZHOU, Xiao Xiong; TORSSELL, Staffan; WALLNER, Olov; SUN, Piaoyang; WO2011/75052; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 90213-67-5, 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. 90213-67-5, name is 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

General procedure: A solution of compound 1 (0.3 mmol) in anhydrous toluene (2 mL)was flushed with Ar, after which Pd(PPh3)2Cl2 (10.5 mg, 0.015 mmol),AsPh3 (18.4 mg, 0.06 mmol) and the corresponding (arylethynyl)tributyltin (0.78 mmol) were added. The mixture was heated at reflux temperature under Ar for 48-72 h. After cooling, the mixture was poured into K2CO3 solution (0.5 M, 20 mL) containing CsF (50mg), stirred for 30 min and extracted with CHCl3. The extract was dried over Na2SO4, filtered and the CHCl3 was removed on a rotary evaporator. The crude residue was purified by column chromatography(CHCl3) to afford pure product 6q-y.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90213-67-5, 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Bucevicius, Jonas; Tumkevicius, Sigitas; Synthesis; vol. 47; 14; (2015); p. 2100 – 2112;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 6299-85-0 ,Some common heterocyclic compound, 6299-85-0, molecular formula is C6H4Cl2N2O2, 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.

44Step 1. To a mixture of 256-dichloro-pyrimidine-4-carboxylic acid methyl ester [1 g, 4.83 mmol, Intermediate (54)] and N,N-diisopropylethylamine (1.27 mL, 7.25 mmol) in THF (16 mL) is added 2- (4-methoxyphenyl)-ethylamine (707 ?L, 4.83 mmol). The resulting mixture is stirred at ambient temperature for 20 hours and poured into 50 mL water and extracted three times with 40 mL ethyl acetate. The organic extracts are combined and washed with 20 mL brine, dried over magnesium sulfate, filtered and concentrated to afford a solid which is purified via flash column chromatography on silica gel (35 g) eluting with 5 to 50% EtOAc in heptane gradient to afford 2-chloro-6-|”2-(4- methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester [1 g, 64.5%, Intermediate (55)]. LCMS: Rx = 2.9 minutes, MS: 322 (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,6299-85-0, its application will become more common.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2006/44732; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
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. 127958-10-5, name is 2-Methyl-4-phenylpyrimidine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. Computed Properties of C12H10N2O2

Example 17: To a mixture of A-14 (135 mg, 0.63 mmol), B-1 (150 mg, 0.53 mmol) and DIPEA (273 mu, 1 .60 mmol) in dry ACN (2.0 mL) is added CIP (191 mg, 0.68 mmol) and the mixture is stirred at RT for 2 days. ACN/H20 is added and the mixture is purified by prep. HPLC-MS (using a solvent gradient H20/ACN with NH4OH) to afford 133 mg of Example 17. ESI-MS: 445 [M+Na]+; HPLC (Rt): 1 .04 min (method G).

The synthetic route of 127958-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; SCHEUERER, Stefan; (69 pag.)WO2017/178341; (2017); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 145783-15-9, 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, 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, name: 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, blongs to pyrimidines compound. name: 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine

3) Operation process(1) Add 18L of ethylene glycol and 9.335kg of SM1 to the 100L reactor.12kg SM2 and 16.529kg triethylamine,Stir and mix;(2) heating the reaction solution to 90 ~ 100 C, the reaction liquid solid dissolved, the color is a yellow clear solution; maintaining this temperature for 8 to 10 hours;(3) TLC detection, the developing agent is ethyl acetate: methanol = 1:1, the color developing agent is ninhydrin ethanol solution, and the color is baked at 150 C;Lower the reaction solution to below 50 C,The reaction solution is a dark brown clear solution;The reaction solution was poured into a 200 L reaction vessel containing 50 L of ethyl acetate and 50 L of water under stirring at room temperature;The 100 L reaction kettle was rinsed with 10 L of ethyl acetate and 10 L of purified water.The eluent was poured into a 200 L reaction kettle; stirred at room temperature for 30 minutes; the stirring was stopped, and the layer was allowed to stand.Divide the lower aqueous phase;(4) Add 60 L of purified water to the upper organic phase, stir at room temperature for 30 minutes; stop stirring, let stand for stratification, and separate the lower layer.water box;(5) Transfer the upper organic phase to a 500L reactor and heat to 60-70 C with stirring; in addition, 180 L of isooctane pre-Heat to 60 ~ 70 C, added to the reaction flask;(8) After adding, slowly cool down to room temperature with stirring and firstly cool to 35-45 C (solid precipitation temperature about 30-35 C).Slowly cool down to 20 ~ 30 C; keep stirring at 20 ~ 30 C for 1 hour, and then slowly reduce the temperature to 0 ~ 10 C;(8) stirring at 0 to 10 C for 2 hours;(9) Centrifugal filtration, the reaction kettle and filter cake are mixed with 12 L of ethyl acetate pre-cooled to 0-10 C and 36 L of isooctane.Rinsing(10) The filter cake is dried under vacuum at 45-55 C for 12 to 16 hours to obtain a white powder of Im-1, weighing 11 kg, yield80%.

The synthetic route of 145783-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hebei Kaiwei Pharmaceutical Co., Ltd.; Pang Yuning; (23 pag.)CN108276417; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
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. 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, the common compound, a new synthetic route is introduced below. Recommanded Product: 1211443-61-6

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.

The synthetic route of 1211443-61-6 has been constantly updated, and we look forward to future research findings.

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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Pyrimidine – Wikipedia

Related Products of 15783-48-9, 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 15783-48-9, name is 2,4-Dichlorofuro[3,4-d]pyrimidin-7(5H)-one. This compound has unique chemical properties. The synthetic route is as follows.

2,6-Dihydroxypyrimidine-4-carboxylic acid (100 g, 73.4 mmol) and paraformaldehyde (84 g, 293 mmol) were combined with concentrated HCl (1.5L) and heated to reflux at 85-95 C for 18 hours. The reaction was then cooled and HCl was evaporated under reduced pressure to obtain a solid. The solid was washed with petrolium ether to give crude 2,4-dihydroxyfuro[3,4- d]pyrimidin-7(5H)-one (90 g, 83 % yield) which was used next tep without further purification.[0113] A mixture of 2,4-dihydroxyfuro[3,4-d]pyrimidin-7(5H)-one (lOOg, 595mmol), phosphoryl trichloride (800mL) and N,N-diethylaniline (150 mL) was heated at 110 C for 18 hours. The reaction was cooled to ambient temperature, the solvent was removed in vacuo to give a residue. The residue was purified on a silica gel column eluted with petroliumether_EtOAc=5: l to give 2,4-dichlorofuro[3,4-d]pyrimidin-7(5H)-one (70 g, 57 % yield) as an off-white solid.[0114] A solution of 2,4-dichlorofuro[3,4-d]pyrimidin-7(5H)-one (34g, 165mmol) in DCM (770 mL) was added 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (24 g, 165 mmol) was cooled to 0 C and then triethylamine (96 mL, 660mmol) was added dropwise. The mixture was then concentrated in vacuo to give a residue which was purified on a silica gel column eluted with DCM_EtOAc=l :2 to give 4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chlorofuro[3,4-d]pyrimidin- 7(5H)-one (28 g, 82% yield) as a yellow solid. MS [M+H] found 282.[0115] Under a nitrogen at 0 titanium chloride triisopropoxide (1 M in hexanes) (75 ml, 75 mmol) was added to a solution of 4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chlorofuro[3,4- d]pyrimidin-7(5H)-one (19 g, 68 mmol) in THF (100 mL) followed by dropwise addition of ethylmagnesium bromide (1 M in THF) (150 ml, 150 mmol). The reaction was warmed up to ambient temperature and stirred overnight and then quenched by addition of a saturated NH4C1 solution (200 mL). The water layer was extracted with ethyl acetate, and the combined organic layers were dried over Na2S04, filtered, and evaporated in vacuo to give a residue. The residue was purified on a silica gel column eluted with petrolium ether_EtOAc=3: l to give l-(6-(8-oxa- 3-azabicyclo[3.2.1 ]octan-3-yl)-2-chloro-5-(hydroxymethyl)pyrimidin-4-yl)cyclopropanol (5 g, 24% yield) as a yellow solid. MS [M+H] found 312.[0116] To a solution of l-(6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-5- (hydroxymethyl)pyrimidin-4-yl)cyclopropanol (3 g, 9.6 mmol) and PPh3(2.5 g,14.4 mmol) in dry THF (200 mL) was added DEAD (3.77 g,14.4 mmol) dropwise at 0 C. The mixture was stirred at ambient temperature for 3 hours. The solvent was removed in vacuum to give a residue which was purified on silica gel column eluted with petroleum ether_EtOAc=4: l to give a residue which was further purified by Prep HPLC (Column: Fuji CI 8 (300×25); Wavelength 220 nm; Mobile phase: A MeCN (0.1% TFA); B water (0.1% TFA); Flow rate: 25 mL /min; Injection volume: 2 mL; Run time: 20 min; Equilibration: 3 min) to give 4′-(8-oxa-3- azabicyclo[3.2.1 ]octan-3-yl)-2′-chloro-5’H-spiro[cyclopropane- 1 ,7′-furo[3,4-d]pyrimidine] (330mg, 12% yield). MS [M+H] found 294.[0117] A mixture of 4′-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2′-chloro-5’H-spiro[cyclopropane- l,7*-furo[3,4-d]pyrimidine] (10.2 mg, 0.035 mmol), l-Methyl-3-[4-(4,4,5,5-Tetramethyl-l,3,2- dioxaborolane-2-yl)phenyl]-urea (19.18 mg, 0.069 mmol), sat. NaHC03 aq. (0.25 ml, 0.035 mmol) and PdCl2(dppf)-CH2Cl2 (2.269 mg, 2.78 muiotaetaomicron) in 1 ,4-Dioxane (0.5 ml) was heated by microwave at 110 C for 30 min. The mixture was passed throught filter and washed with MeOH. The filtrate was purified by preparative HPLC (gradient 20-45% ACN (containing 0.035% TFA) in water (containing 0.05% TFA). The fractions containing the desired compound were combined and concentrated in vacuo to give a solid. This solid was partitioned between EtOAc and NaHC03 aq. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaCl, dried and concentrated in vacuo to give a beige solid, which was triturated with hexane/ethyl acetate (1 : 1), collected by filtration, rinsed with hexane/ethyl acetate (1 :1) and dried to give the title compound (10.1 mg, 0.025 mmol, 71.4 % yield) as a beige solid. 1H NMR (400 MHz, DMSO- 6) delta ppm 1.09 (m, 2 H) 1.18 (m, 2 H) 1.78 (m, 4 H) 2.65 (s, 3 H) 3.25 (m, 2 H) 3.95 (m, 2 H) 4.43 (m, 2 H) 5.32 (s, 2 H) 6.12 (br s, 1 H) 7.47 (d, J=8 Hz, 2 H) 8.14 (d, J= 8 Hz, 2 H) 8.81 (s, 1 H). MS [M+H] found 408.

According to the analysis of related databases, 15783-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; JIN, Bohan; LARDY, Matthew; ZHOU, Feng; DONG, Qing; WO2012/99581; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 90213-67-5, 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 90213-67-5, name is 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Sonogashira Coupling; Compound 2a: A solution of 1(400 mg, 1.98 mmol) in anhyd Et3N (20 mL) was flushed withargon and Pd(PPh3)2Cl2 (28.0 mg, 0.04 mmol), PPh3 (21.0 mg,0.08 mmol), CuI (3.8 mg, 0.02 mmol) and phenylacetylene (260muL, 2.38 mmol) were added. The mixture was stirred underargon at 60 C for 2-3 h. After cooling, the reaction mixture waspoured into H2O (40 mL) and extracted with CHCl3. The extractwas dried over Na2SO4, filtered and the solvent removed byrotary evaporation. The residue was purified by column chromatography(eluent CHCl3) and recrystallized to give compound 2a.

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 90213-67-5, 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Bucevicius, Jonas; Tumkevicius, Sigitas; Synlett; vol. 26; 6; (2015); p. 810 – 814;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1152475-42-7, 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 1152475-42-7, name is 7-Bromo-2-chlorothieno[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 1-h (671 mg, 1.64 mmol), 2-(methanesulfonyl)phenylboronic acid (328 mg, 1.64 mmol), bis(triphenylphosphine)palladium(II) dichloride (69 mg, 0.09 mmol) 2-di-tert-butylphosphino- 2?,4?,6?-triisopropylbiphenyl (63 mg,0.15 mmol) and 2 M aqueous sodium carbonate solution (6.5 mL, 13 mmol) were dissolved in 1,4-dioxane (13 mL). Thereaction mixture was replaced with nitrogen three times to remove the oxygen inside the system and then heated at90C for 6 hours. The reaction was cooled to room temperature, diluted with ice water (100 mL) and extracted withdichloromethane (100 mL 3 3). The combined organic phases were washed successively with water (50 mL 3 3) andbrine (50 mL),dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure.The residue was purified by silica gel thin layer chromatography preparative plate (dichloromethane: methanol = 40: 1)to deliver a yellow solid 5-b (130 mg, yield: 24%). LC-MS (ESI): m/z = 325 [M+H]+.

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 1152475-42-7, 7-Bromo-2-chlorothieno[3,2-d]pyrimidine.

Reference:
Patent; Guangzhou Maxinovel Pharmaceuticals Co., Ltd.; ZHANG, Nong; XU, Zusheng; WANG, Tinghan; WANG, Yuguang; (99 pag.)EP3287463; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 31169-25-2, 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. 31169-25-2, name is 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one, molecular formula is C6H3BrN2OS, 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.

7-Bromothieno[3,2-d]pyrimidine-4(3H)-one (5.9g) was dissolved in POCl3 (20mL) and then stirred at 150C for 3 hours. After cooling down to room temperature, the remaining POCI3 was concentrated and added to ice water to obtain a solid. The solid was washed with sat. NaHC03 solution and dried with N2 gas to obtain the title compound. NMR (400MHz, DMSO-d^) delta 9.16 (s, 1H), 8.79 (s, 1H).

According to the analysis of related databases, 31169-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANMI HOLDINGS CO., LTD.; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; CATHOLIC UNIVERSITY INDUSTRY ACADEMIC COOPERATION FOUNDATION; SON, Jung Beom; JUNG, Seung Hyun; CHOI, Wha Il; JUNG, Young Hee; CHOI, Jae Yul; SONG, Ji Yeon; LEE, Kyu Hang; LEE, Jae Chul; KIM, Eun Young; AHN, Young Gil; KIM, Maeng Sup; CHOI, Hwan Geun; SIM, Tae Bo; HAM, Young Jin; PARK, Dong-sik; KIM, Hwan; KIM, Dong-Wook; WO2011/93684; (2011); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia