Pyrimidines

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;,
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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;,
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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;,
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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;,
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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;,
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Pyrimidine – Wikipedia

Related Products of 124703-78-2 , The common heterocyclic compound, 124703-78-2, name is 6-Ethylpyrimidin-4(3H)-one, molecular formula is C6H8N2O, 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.

(ii) 4,5-Dichloro-6-ethylpyrimidine To a solution of 6-ethylpyrimidin-4(3H)-one (the product of part (i)) (18.6 g, 150 mmol) in concentrated hydrochloric acid (120 ml) at 30-40 C. was added dropwise a 30 wt. % solution of hydrogen peroxide in water (18 ml) over a period of 30 minutes (slight exotherm resulted) and the resulting mixture was stirred overnight at 40 C. The mixture was concentrated under reduced pressure and the residue was suspended/dissolved in toluene and the toluene removed under reduced pressure. The residue was dissolved in phosphorus oxychloride (150 ml) and heated under reflux for 3 hours after which time the excess phosphorus oxychloride was removed under reduced pressure. The residue was poured into ice/water, extracted with methylene chloride (3*50 ml) and the combined organic extracts were washed with water (30 ml) and dried over magnesium sulphate. The solvent was removed under reduced pressure and the resulting oil was distilled under reduced pressure to yield the title compound (5.4 g, 20%), b.p. 104 C. at 22 mm Hg, which was characterised by 1 H-NMR spectroscopy. 1 H-NMR (CDCl3): delta=1.3 (t, 3H, J=10Hz), 3.04 (q, 2H, J=10Hz), 8.75 (s, 1H), ppm.

The synthetic route of 124703-78-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US5278175; (1994); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3435-25-4 , The common heterocyclic compound, 3435-25-4, name is 4-Chloro-6-methylpyrimidine, molecular formula is C5H5ClN2, 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.

BA-1 (1.00 g, 7.78 mmol) and Ni(dppe)Cl2 (82 mg, 0.16 mmol)The solution in anhydrous Et 2 O (5 mL) was cooled to -10 C.A solution of cyclopropylmagnesium bromide (1.36 g, 8.56 mmol) was added dropwise and the mixture was stirred at -10 C for 2 h.The mixture was quenched with saturated aqueous NH4CI, extracted with DCM and concentrated. The crude BD-1 can continue to be used without further processing.

The synthetic route of 3435-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BAKONYI,JOHANNA; BRUNETTE,STEVEN RICHARD; COLLIN,DELPHINE; HUGHES,ROBERT OWEN; LI,XIANG; LIANG,SHUANG; SIBLEY,ROBERT; TURNER,MICHAEL ROBERT; WU,LIFEN; ZHANG,QIANG; (169 pag.)TW2018/38997; (2018); A;,
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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. 7752-72-9, name is 5-Chloro-6-methylpyrimidin-4(3H)-one, the common compound, a new synthetic route is introduced below. Product Details of 7752-72-9

2) Preparation of 4,5-dichloro-6-methylpyrimidineThe 14.5g (0.1mol) 4-hydroxy-5-chloro-6-methylpyrimidine dissolved in 50ml of toluene, was added dropwise with stirring to the reaction flask 50ml of phosphorus oxychloride dropwise at reflux temperature the reaction completion 5-7 hours after, TLC monitored the reaction is complete. The toluene was evaporated under reduced pressure and an excess of phosphorus oxychloride, while stirring the reaction was poured into ice water, the aqueous phase was extracted with (3 ¡Á 50ml) and extracted with ethyl acetate, the combined organic phase was dried over anhydrous magnesium sulfate, filtered, desolvation . The residue was purified by column chromatography (eluent, ethyl acetate and petroleum ether (boiling range 60-90 ), the volume ratio of 1: 4) was isolated as a yellow liquid 14.43g, yield 88.5%.

The synthetic route of 7752-72-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenyang SinochemAgrochemicals R&D Co., Ltd.; Liu, Zhangling; Xu, Ying; Wang, Junfeng; Sun, Xufeng; Ban, Lanfeng; Xie, Yong; Li, Zhinian; Sun, Geng; (59 pag.)CN105348298; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 90213-66-4 ,Some common heterocyclic compound, 90213-66-4, molecular formula is C6H3Cl2N3, 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 stirred solution of compound (XXIX, 50 g) in DMF (200 mL) was added N-iodosuccinimide (62.14 g) and stirred for 16 hrs. The reaction mixture was poured slowly into water (3.5 L) resulted in precipitation which was filtered, washed with water (1 L) and suck dried. Crude residue was purified by refluxing in ethyl acetate and filtered to give compound(XXX).

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. 90213-66-4, 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUN PHARMA ADVANCED RESEARCH COMPANY LIMITED; KADIYALA, V.S.N. Murty; DESAI, Dipali Manubhai; RAUT, Virendra Narendra; SAVANT, Pratit Viram; JOSHI, Kiritkumar Parmeshkumar; CHAUDHARI, Umesh Vishnu; RATHOD, Rajendrasinh Jashvantsinh; BHATT, Tushar Bhupendrabhai; CHITTURI, Trinadha Rao; (87 pag.)WO2018/2958; (2018); A1;,
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Pyrimidine – Wikipedia