Tag: M.W:200-300

Synthetic Route of 145783-15-9, 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. 145783-15-9, name is 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine. A new synthetic method of this compound is introduced below.

Example 1 Synthesis of 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl]amino]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]ethanol (Compound I) Take 250mL reaction flask, 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (16.1g, 68mmol), 2-[[(3aR, 4S, 6R, 6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-yl]oxy]-1-ethanol-dibenzoyl-L-tartaric acid salt (17.3g, 68mmol), N,N-diisopropylethylamine (34.3g, 340mmol) and n-butanol (49mL). The resulting reaction mixture was sealed and heated to 90 ,The temperature was maintained at 35h.Followed by cooling to 30C. The solvent was distilled off. Isopropyl acetate and water, the phases were separated. The aqueous phase was extracted with isopropyl acetate, the combined organic phases, washed. Dried over anhydrous magnesium sulfate. Filter. The solvent was distilled off, give a reddish brown oil. N-heptane was added after a beating, white solid 24.5g, yield 85.8%. HPLC purity was 98.8%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145783-15-9, its application will become more common.

Reference:
Patent; Qingdao Huanghai Pharmaceutical Co., Ltd.; Zhang, Fuli; Xu, Jianguo; Liu, Xiaohua; Gao, Yongji; He, Xiaoqing; Xu, Taizhi; Hu, Jie; (12 pag.)CN103626745; (2016); B;,
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. 160199-05-3, name is 2,4-Dichlorobenzo[4,5]thieno[3,2-d]pyrimidine, the common compound, a new synthetic route is introduced below. Formula: C10H4Cl2N2S

4,4,5,5-tetramethyl-2- (naphthalen-2-yl) – (4-methylphenyl) pyridine was added to the starting material 2,4-dichlorobenzo [4,5] thieno [3,2- 1,3,2-dioxaborolane (35 g, 138 mmol), Pd (PPh3) 4 (5.80 g, 5.02 mmol), K2CO3 (52 g, 376.41 mmol), THF (440 ml)The temperature of the reaction was raised to 80 DEG C and stirred for 6 hours. After the completion of the reaction, water was removed from the reaction mixture, and the mixture was filtered under reduced pressure, dried over MgSO 4 and concentrated. The resulting compound was purified by silicagel column and recrystallized19.58 g of the product (yield: 45%) was obtained.

The synthetic route of 160199-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duksan Neolux Co.,Ltd.; Samsung Display Co., Ltd.; Yoon Jin-ho; Cho Hye-min; Park Mu-jin; Lee Jeong-uk; Lee Seon-hui; Kim Tae-gyeong; Lee Yun-gyu; Lee Jeong-seop; (41 pag.)KR2018/133276; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 815610-16-3, 2-Amino-4-iodopyrimidine, 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, Product Details of 815610-16-3, blongs to pyrimidines compound. Product Details of 815610-16-3

To a solution of 4-iodopyrimidin-2-amine (400 mg, 1.8 MMOL) in THF (10 mL) was added Pd (PPh3) 2CI2 (63 mg, 0.09 MMOL), Cul (34 mg, 0.18 mmol), TMS-acetylene (510 muL, 3.6 MMOL), and TEA (750 SLL, 5.4 MMOL). The mixture was heated to 50C for 1 hr. The solvent was removed in vacuo. THF (8 mL) and MeOH (1 mL) was added to the crude material followed by KF (313 mg, 5.4 MMOL). The material was concentrated and used crude in subsequent reactions

At the same time, in my other blogs, there are other synthetic methods of this type of compound,815610-16-3, 2-Amino-4-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/16914; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 89581-38-4, Methyl 5-bromopyrimidine-2-carboxylate, 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, Quality Control of Methyl 5-bromopyrimidine-2-carboxylate, blongs to pyrimidines compound. Quality Control of Methyl 5-bromopyrimidine-2-carboxylate

To a mixture of methyl 5-bromopyrimidine-2-carboxylate (2.30 g, 10.6 mmol) and copper (I) cyanide (1.92 g, 21.4 mmol) in a 100 mL round bottom flask was added DMA (21 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 5 min. The reaction mixture was heated to 110 C for 2 d and cooled to room temperature. The reaction mixture was diluted with EtOAc and water and filtered through a glass frit (medium). The filtrate was transferred to a separatory funnel. The aqueous phase was extracted with EtOAc (4 x) and the combined organic extracts were washed with brine (1 x), dried over MgS04, filtered, concentrated to give a yellow oil. Purification by flash column chromatography on silica gel (80 g, 5% to 50% EtOAc in heptane) gave methyl 5-cyanopyrimidine-2-carboxylate (0.83 g, 5.08 mmol, 48 % yield) as a white solid. LC/MS (ESI) m/z = 164.0 (M+H). Calculated for C7H5N3O2 163.0

The synthetic route of 89581-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 145783-15-9, Adding some certain compound to certain chemical reactions, such as: 145783-15-9, name is 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine,molecular formula is C7H9Cl2N3S, 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 145783-15-9.

Compound (1-1) (476 mg, 2.0 mmol), hydrochloric salt of compound (2?) (524 mg, 2.2 mmol) and NaHCO3 (370 mg, 4.4 mmol) were added to DMF (20 ml). Under the nitrogen atmosphere, the reaction mixture was stirred for 12-15 hours at 90-95 . The reaction was monitored by TLC. After completion, water (100 ml) and CH2Cl2 (100 ml) were added to the reaction mixture. The resulting mixture was stirred for 30 min, followed by the separation of the aqueous and organic layers. The dichloromethane layer was washed with water (20 ml*3) until to neutral. The resulting organic layer was dried with anhydrous sodium sulfate, and then filtered. The filtrate was removed by distillation at reduced pressure to obtain crude product (compound (1-c?)). The crude product was crystallized from the mixture of dichloromethane and petroleum ether to obtain a white solid (656 mg, yield 82.0%). HPLC purification is above 98%. (0094) 1HNMR (400 MHz, CDCl3) delta: 6.81 (b, 2H), 4.62-4.72 (m, 2H), 4.51-4.53 (m, 1H), 3.95 (d, J=7.6 Hz, 1H), 3.67-3.82 (m, 3H), 3.63-3.64 (m, 1H), 3.03-3.22 (m, 2H), 2.30-2.33 (m, 1H), 1.92-1.95 (m, 1H), 1.73-1.82 (m, 2H), 1.09 (t, J=7.6 Hz, 3H), MS (m/z): [M+H]+=405.86.

According to the analysis of related databases, 145783-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRIGHTGENE BIO-MEDICAL TECHNOLOGY (SUZHOU) CO., LTD; YUAN, Jiandong; JIANG, Qiao; LI, Xiang; US2015/322071; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 163622-50-2, 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. 163622-50-2, name is 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below.

4-amino-5-iodo-weighed -7H- pyrrolo [2,3-d] pyrimidine (2g, 0.0077mol)And potassium carbonate (4.2 g, 0.0310 mol),After adding DMF (50mL) dissolved and heated to 90 reflux,N-Butyl iodide (2 mL) was added dropwise to the solution using a separatory funnel.After 3 hours of reaction, the solvent was evaporated, extracted with ethyl acetate,The organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure.And purified by column chromatography to give 1.80 g of a white solid (74% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,163622-50-2, 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Sichuan University Huaxi Hospital; He Yang; Chai Yingying; Chen Bojiang; Zhou Xinglong; Li Changfu; Qiu Zhixin; Li Weimin; (11 pag.)CN106831790; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5909-24-0 ,Some common heterocyclic compound, 5909-24-0, molecular formula is C8H9ClN2O2S, 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.

In DCM (100 mL) were dissolved ethyl 4-chloro-2-(methylthio) pyrimidine-5-carboxylate (5.0 g, 21.55 mmol), 3-chloro-4-methoxybenzylamine (4.0 g, 23.4 mmol) and triethylamine (4.35 g, 43.1 mmol). The reaction mixture was stirred at ambient temperature for 10 h and washed with water. The organic phase was dried over magnesium sulfate and concentrated to give ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2 -(methylthio)pyrimidine-5-carboxylate as a solid (6.0 g, 76 % 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. 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; WANG, Aichen; EP2886540; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 32779-37-6 , The common heterocyclic compound, 32779-37-6, name is 2,5-Dibromopyrimidine, molecular formula is C4H2Br2N2, 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.

11126] To a solution of intermediate B-S (520 g, 2.45 mmol) in DMA (8.2 mE) was added DIPEA (0.84 mE, 4.90 mmol) followed by 2,5-dibromopyrimidine (661 g, 2.69 mmol). The reaction mixture was heated at 120 C. for 30 minutes using microwave and was then diluted with water and EtOAc. The aqueous phase was extracted twice with EtOAc and the combined organic layers were washed with a saturated solution of NaC1, dried over Mg504, filtered and evaporated. Purification via silica gel chromatography (0-40% EtOAc in hexanes) gave the title compound (651 g, 72%). MS (ESI): mass calcd. for C,5H2,BrN4O2, 368.1; m/z found, 370.9 [M+H]. ?H NMR (500 MHz, CDC13) oe 8.28 (is, 2H),5.56 (s, 1H), 4.29 (s, 1H), 4.23-4.15 (m, 1H), 3.99-3.91 (m, 1H), 2.03-1.93 (m, 1H), 1.87-1.63 (m, 2H), 1.62-1.32 (m, 12H).

The synthetic route of 32779-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; COATE, Heather R.; DVORAK, Curt A.; FITZGERALD, Anne E.; LEBOLD, Terry P.; PREVILLE, Cathy; SHIREMAN, Brock T.; (473 pag.)US2016/46640; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 89581-38-4, 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.89581-38-4, name is Methyl 5-bromopyrimidine-2-carboxylate, molecular formula is C6H5BrN2O2, molecular weight is 217.0201, as common compound, the synthetic route is as follows.

To the reaction flask were added 1 mmol of compound F55, N, N-dimethylglycine, cuprous iodide, Cs2CO3, 1, 4-Dioxane and 2 mmol of 5-bromo-2-pyrimidinecarboxylic acid methyl ester, heating under nitrogen to 80 C for 24 h,Water, extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified on a silica gel column(Eluent: petroleum ether: ethyl acetate = 1: 1) to give the title product as a pale yellow oily liquid.

The chemical industry reduces the impact on the environment during synthesis 89581-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangdong Zhongsheng Pharmaceutical Co., Ltd.; Chen, Lijuan; Long, Chaofeng; Chen, Xiaoxin; Liu, Zhuowei; Ye, Haoyu; Xie, Chengshi; (104 pag.)CN106045923; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4319-77-1, 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 4319-77-1 as follows.

C. Preparation of 4,6-dimethoxy-5-(pyridin-4-yl)pyrimidine A mixture of 5-bromo-4,6-dimethoxypyrimidine (2.18 g, 10 mmol), pyridine-4-boronic acid (1.85 g, 15 mmol), K2CO3 (2.76 g, 20 mmol), and PXPd (539 mg, 1.0 mmol) in ethanol/THF (1:1, 25 mL) under argon was heated at 70 C. for 3 h. Analysis by HPLC/MS indicated that the reaction was complete. After the reaction mixture was cooled to room temperature, the solvent mixture was removed under reduced pressure. The residue was dissolved in EtOAc (30 mL) and washed with saturated aqueous NaCl (20 mL), then dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography eluted with ethyl acetate-hexanes to obtain the title compound (1.79 g) as a white solid. 1H NMR (CDCl3): delta 3.97 (s, 6H), 7.36 (d, 2H), 8.47 (s, 1H), 8.64 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4319-77-1, its application will become more common.

Reference:
Patent; Wu, Gang; Mikkilineni, Amarendra B.; Sher, Philip M.; Murugesan, Natesan; Gu, Zhengxiang; US2006/287341; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia