Day: May 11, 2021

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

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 3764-01-0, 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 3764-01-0 as follows.

2,4,6-Trichloropyrimidine (5.5 mL, 48.0 mmol) was dissolved in tetrahydrofuran (70 mL).Then, palladium acetate (0.147 g, 0.64 mmol) was sequentially added thereto.Triphenylphosphine (353 mg, 1.28 mmol),p-Methoxybenzeneboronic acid (5.01 g, 31.9 mmol)And aqueous sodium carbonate (1M, 64 mL, 64 mmol),The resulting mixture was heated to 60 C under a nitrogen atmosphere and stirred for 6 hours.Cool to room temperature, concentrate under reduced pressure to remove organic solvent.Water (100 mL) was added to the residue.The resulting mixture was extracted with ethyl acetate (100 mL¡Á3).The combined organic phases were washed with brine (100 mL).Dry anhydrous sodium sulfate, filter, and concentrate the filtrate to dryness.The residue was purified by EtOAc EtOAc EtOAc(5.58g, 68%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3764-01-0, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; (138 pag.)CN108276401; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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

Synthetic Route of 705263-10-1 ,Some common heterocyclic compound, 705263-10-1, molecular formula is C6H4BrN3, 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.

The mixture of 15a (0.87 g, 4.39 mmol), 4-[4-(tert- butoxycarbonyl)piperazin-l-yl]phenylboronic acid pinacol ester (1.7 g, 4.39 mmol), Pd(Ph3P)4 (0.5 g, 0.439 mmol), K2CO3 (1.82 g, 13.17), 1 ,4-dioxane (15 mL) and H2O (5 mL) was heated at 1 10 C under a nitrogen atmosphere for 5 h in a sealed vial. The reaction mixture was concentrated and the residue was purified by column chromatography using CH2Cl2/EtOAc to give 16 (1.4 g, 86% yield). 1H NMR (CDCl3) delta 8.82 (dd, J = 2.2, 0.7 Hz, IH), 8.77 (d, J = 2.2 Hz, I H), 8.16 (d, J = 2.2 Hz, 1 H), 7.54 (d, J = 8.8 Hz, 2H), 7.08 (d, J = 8.8 Hz, 2H), 6.75 (dd, J = 2.2, 0.7 Hz, 1 H), 3.63 – 3.67 (m, 4H), 3.25 – 3.28 (m, 4H), 1.53 (s, 9H).

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. 705263-10-1, 6-Bromopyrazolo[1,5-a]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; THE BRIGHAM AND WOMEN’S HOSPITAL, INC.; WO2009/114180; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 157335-93-8 , The common heterocyclic compound, 157335-93-8, name is 4,6-Dimethylpyrimidine-5-carboxylic acid, molecular formula is C7H8N2O2, 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 solution of 12 (0.24 g, 0.70 mmol) in DCM (10 mL) were added 4,6-dimethyl- pyrimidine-5-carboxylic acid (55, 0.12 g, 0.84 mmol) , EDCI (0.17 g, 0.91 mmol), HOBt (0.12 g, 0.91 mmol) and DIPEA (0.36 mL, 2.10 mmol). The mixture was stirred at RT for 3 h. The reaction mixture was washed with saturated NaHC03 and the organic layer was dried (Na2S04). The crude product was purified by SiOz column chromatography eluting with DCM:MeOH:NH40H (150:10:1) to afford 0.27 g (81 %) of I-29:: mp 48.0- 49.0 C; ms (ES+) m/z 476 (M + H) ; Anal. (C28H37N502, 0.2M CH2Cl2) C; calcd, 68.76; found, 68.61; H; calcd, 7.65; found, 7.51; N; calcd, 14.22; found, 14.28

The synthetic route of 157335-93-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2005/121145; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 2915-16-4, 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 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

20 g of 11-(3-(dibenzo[b,d]furan-4-yl)phenyl)-11,12-dihydroindole[2,3-a]carbazole,4. A mixture of 8 g of sodium hydride and 300 ml of toluene in a 1 liter flask,And stirred at 40 C under a nitrogen atmosphere. After one hour,Add 12. 8 g of 2-chloro-4,6-diphenyl-1,3-pyrimidine,And continue to stir at 80 C. The reaction was monitored by thin layer chromatography.After completion of the reaction, the reaction mixture was quenched with 200 ml of water,And extracted with 150 ml of ethyl acetate. The organic layer was extracted with 100 ml of water three times and dried over anhydrous sodium sulfate. The collected ethyl acetate layer was further purified by celite column chromatography. The ethyl acetate layer is followed by a rotary evaporatorIn the vacuum was evaporated to dry. The residue was further precipitated by the addition of 100 ml of n-hexane, and 18 g of a yellow solid compound F5 (85% yield) having more than 99% HPLC purity was obtained under vacuum.

According to the analysis of related databases, 2915-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; e-Ray Optoelectronics Technology Co., Ltd; Balaganesan, Banumathy; HUANG, HEH LUNG; KAU, HUANG MING; HSU, PO WEI; (22 pag.)CN106608878; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1004-39-3, 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 1004-39-3 as follows.

To a flask equipped with a magnetic stirrer added 4,6-diamino-2-mercaptopyrimidine (1.4218g, 0.01mmol). It was dissolved in 40mL of methanol and added 42mL 0.25M aqueous sodium hydroxide solution. The above aqueous solution was added to the flask and stirred for 2.5 hours at room temperature to give the sodium salt of a mercapto group. After completion of the reaction, Vacuum distillation and Vacuum drying was used overnight. The dried Mercapto sodium salt was dissolved in 62mL of N, N- dimethylformamide (DMF) and Added in Step 2) obtained 4′-(1-bromo-4-butoxy)-4-cyanoazobenzene (3.9820g, 0.11mmol), stirred at room temperature for 20h. After completion of the reaction, ethyl acetate was added then dried overnight over anhydrous magnesium sulfate, filtered, Rotary evaporated to remove residual solvent. The crude product was further purified by silica gel column chromatography and finally get a diamine containing Azo-Pyrimidine monomer

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1004-39-3, its application will become more common.

Reference:
Patent; Yidun New Materials (Suzhou) Co., Ltd.; Lu, Qinghua; Tong, Faqin; (24 pag.)CN105693625; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 65996-58-9, 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. 65996-58-9, name is 2-Amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one. A new synthetic method of this compound is introduced below.

Amixture of 9-deazapurine 5 (150.0 mg, 1.0 mmol) and benzoylchloride (2.2 equiv) in trifluoromethanesulfonic acid (3.45 g,23 mmol) was stirred at 80-120 C for 48 h. After the mixturewas cooled and H2O (15 mL) was added. Then the reaction wasneutralized with NaOH 1.0 mol/L, the volume adjusted to approximately35 mL by adding H2O and then 60 equiv of NaOH wereadded. The reaction was stirred for 2.5 h at 60 C. The mixturewas neutralized with glacial acetic acid and the formed solid wasfiltered under vacuum and washed several times with dichloromethane(10 mL), ethyl acetate (10 mL), acetone (5 mL) andmethanol (5 mL). The precipitate purity was monitored by CCDand depending on the product, further purification was necessaryby recrystallization in methanol or flash chromatography usingCH2Cl2/MeOH (4:1) as eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65996-58-9, 2-Amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one, and friends who are interested can also refer to it.

Reference:
Article; Rodrigues, Marili V.N.; Barbosa, Alexandre F.; Da Silva, Julia F.; Dos Santos, Deborah A.; Vanzolini, Kenia L.; De Moraes, Marcela C.; Correa, Arlene G.; Cass, Quezia B.; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 226 – 231;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 42754-96-1, 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 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4,6-dichloro-1H-pyrrolo[3,4-d]pyridine (110 mg, 0.58 mmol) in DMF (5 mL) was added K2C03 (160 mg, 1.16 mmol). Then the reaction mixture was stirred for 30 mm maintaining at temperature, then iodomethane (3.78 g, 26.60 mmol) was added. The reaction mixture was stirred at rt overnight. Water (50 mL) was added to quench the reaction, and the resulting mixture was extracted with EtOAc (50 mL x 2). The combined organic phases were washed with saturated brine (80 mL), dried over anhydrous Na2504, filtered, and the filtrate was concentrated in vacuo.The residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 10/i) to give the title compound as a yellow solid (48 mg, 41 %).?HNIVIR (400 IVIFIz, CDC13) (ppm): 8.16 (s, 1H), 4.13 (s, 3H).

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 42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; REN, Qingyun; TANG, Changhua; YIN, Junjun; YI, Kai; ZHANG, Yingjun; (264 pag.)WO2018/33082; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia