Pyrimidines

3934-20-1, 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 3934-20-1 as follows.

Phenylboronic acid (1 eq) and 2,4-dichloropyrimidine (1 eq) were added to tetrahydrofuran, to which 10% sodium bicarbonate (1 eq) was added. Nitrogen was bubbled into the mixture to remove oxygen while the reaction mixture was well stirred. 0.05 equivalent of palladium tetrakis was added to the mixture and stirred well. The mixture was then refluxed under a stream of nitrogen for 24 hours. After the reaction was complete, the mixture was worked up with ethyl acetate and water to give a crude yellow solid. The solid was purified by column chromatography to give white solid crystals. TLC was observed at Rf: 05 (ethyl acetate: hexane)

The chemical industry reduces the impact on the environment during synthesis 3934-20-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHUNGNAM NATIONAL UNIVERSITY INDUSTRY & ACADEMIC COOPERATION (IAC); JUNG, SANG HUN; WOO, SUN HEE; KIM, SANG KYUM; JEON, EUN SEOK; LEE, YOU JUNG; MANICKAM, MANOJ; JALANI HITESHKUMAR, HITESHKUMAR; SHARMA, NITI; (234 pag.)KR2015/111825; (2015); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

7504-94-1, 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 7504-94-1, name is 2-Hydrazinylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

After adding 230 mg of 2-hydrazinopyrimidine and 293 mul of triethylamine to a 50 ml DMF solution containing 983 mg of {2-(3-ethoxy-4-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester, the mixture was stirred at 85 C. for 10 hours under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 30 ml of a methanol_THF=1:1 mixed solvent. After adding 420 mul of acetic acid and 657 mg of sodium cyanotrihydroborate to the reaction mixture, it was stirred at room temperature for 5 hours. Ethyl acetate was added to the reaction mixture which was then filtered through a small amount of NAM silica gel, and the silica gel was washed with ethyl acetate-methanol. The filtrate was concentrated under reduced pressure, and the residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate) to give the title compound (400 mg) as a light yellow solid. 1H-NMR (CDCl3) delta 1.32 (t, J=7.2 Hz, 3H) 2.58 (s, 3H) 3.80 (s, 3H) 3.90 (q, J=7.2 Hz, 2H) 5.77 (d, J=7.2 Hz, 1H) 6.77 (d, J=8.8 Hz, 1H) 6.83 (d, J=8.8 Hz, 2H) 7.12-7.17 (m, 3H) 7.81 (d, J=8.8 Hz, 2H) 8.69 (d, J=4.8 Hz, 2H)

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 7504-94-1, 2-Hydrazinylpyrimidine.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2008/15199; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

93366-88-2, 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. 93366-88-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-2-amine. A new synthetic method of this compound is introduced below.

7H-pyrrolo[2,3-d]pyrimidin-2-amine (388 mg, 2.90 mmol), 4-bromo-2-iodo-1-methoxybenzene (2.56 g, 8.64mmol), potassium carbonate (1.66) Mg, 12.03 mmol) and valine (83 mg, 0.72 mmol) were added to an eggplantflask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (60 mg, 0.31mmol) was added and the reaction solution was deoxygenated. Heat to 90C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixturewas filtered over Celite. The target compound was obtained in 60 mg.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,93366-88-2, 7H-Pyrrolo[2,3-d]pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

62802-42-0 ,Some common heterocyclic compound, 62802-42-0, molecular formula is C4H2ClFN2, 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 large microwave vial was charged with potassium (2Z)-2-buten-2-yltrifluoroborate (Sigma- Aldrich, 900 mg, 5.6 mmol), potassium phosphate (3.54 g, 16.7 mmol) and 2-chloro-5- fluoro-pyrimidine (686 ^L, 5.6 mmol). DMF (10 mL) and water (2 mL) were added and the mixture was deoxygenated with an Ar stream. Tetrakis(triphenylphosphine)palladium (642 mg, 0.56 mmol) was added, and the slurry was again deoxygentaed with an Ar stream. The vial was then capped and heated in the microwave at 95 C for 12 h. The reaction mixture was then partitioned between water (60 mL) and diethyl ether (2X). The combined organic layers were washed with water (1X) and brine (1X), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent: pure DCM) to provide 403.1 (476 mg, 56% yield) as a light yellow oil. LCMS-ESI (pos.) m/z: 153.2 (M+H)+.

According to the analysis of related databases, 62802-42-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Some common heterocyclic compound, 54-20-6, molecular formula is C5H3F3N2O2, 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.54-20-6

EXAMPLE 9 Into a mixture of 5.0 g of 5-trifluoromethyluracil, 2.9 g of 2,3-dihydrofuran and 0.3 g of triethylamine in 40 ml of dioxane kept at 15 C. under agitation was added 7.5 g of dimethyldichlorosilane as a portion and the reaction was continued for about 2 hours with agitation. The treatment procedure after completion of the reaction was much the same as in Example 1 to give 5.0 g of a crystalline product of N1 -(2-tetrahydrofuryl)-5-trifluoromethyluracil having a melting point of 208 C. The yield was 72.0% of the theoretical.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 54-20-6.

Reference:
Patent; Toshin Chemical Co., Ltd.; US4159378; (1979); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

873-83-6, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 873-83-6, name is 6-Aminopyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Synthesis of 7H-pyrrolo[2,3-d]pyrimidine-2,4-diol To a suspended solution of 6-aminouracil (12.7 g, 100 mmol) and sodium acetate (8.2 g, 100 mmol) in H2O (100 mL) at a temperature of 70-75¡ã C., was added a solution of chloroacetaldehyde (50percent in water, 23.6 g, 150 mmol). The resulting reaction mixture was stirred at 80¡ã C. for 20 min, and then cooled to room temperature. The separated solid was collected by filtration, washed with water and acetone, and dried in vacuum to give the title compound as brown solid (14.74 g, 98percent yield). MS(ESI, M-1) m/z 150.2.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 873-83-6, 6-Aminopyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Wyeth; US2010/3250; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

672-41-3, 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. 672-41-3, name is 6-(Trifluoromethyl)pyrimidin-4-amine, molecular formula is C5H4F3N3, 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.

Add the amine obtained in Step 1 (550 mg, 3.37 mmol), Et3N (680 mg, 6.74 mmol) to THF (10 mL), cool to 0 C. on ice bath. Add slowly a solution of phenyl chloroformate (789 mg, 5.06 mmol) in THF. After addition, stir the reaction on ice bath for 20 hrs. Remove the volatiles under reduced pressure. Purification by chromatography (silica gel, EtOAc_PE=1:3) affords the target compound (160 mg, 17%). MS: (M+1): 284.1.

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. 672-41-3, 6-(Trifluoromethyl)pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

75833-38-4, 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 75833-38-4 as follows.

A mixture of 2-chloropyrimidine-4-carbonitrile (1 .5 g, 10.7 mmol), di-tert-butyldicarbonate (2.8 mL, 12.9 mmol) and 10% Pd/C (572 mg, 0.5 mmol) in EtOH(25 mL) was stirred at room temperature under a hydrogen atmosphere (1atm, balloon). After 4h, the reaction mixture was filtered through a pad ofCelite. The filtrate was concentrated under vacuum. Purification (FCC, 5i02, 0-99% EtOAc) to yield title product (720 mg, 27%). MS (ESI): mass calcd. forC10H14C1N302, 243.7; mlz found, 187.9 [M-t-Bu]. 1H NMR (400 MHz, DMSOd 5) O 8.72 (d, J= 5.1 Hz, 1H), 7.56 (t, J= 6.2 Hz, 1H), 7.39 (d, J= 5.1 Hz, 1H),4.21 (d, J = 6.0 Hz, 2H), 1.40 (5, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75833-38-4, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHEN, Gang; CHROVIAN, Christa C.; COATE, Heather R.; DVORAK, Curt A.; GELIN, Christine F.; HISCOX, Afton; LETAVIC, Michael A.; RECH, Jason C.; SOYODE-JOHNSON, Akinola; STENNE, Brice; WALL, Jessica L.; ZHANG, Wei; (583 pag.)WO2017/139428; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

7461-50-9, 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. 7461-50-9, name is 2-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, 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.

2-Chloropyrimidin-4-ylamine (3.5 g, 27.0 mmol), 4-methoxypiperidine hydrochloride (4.09 g, 27.0 mmol) and cesium carbonate (26.4 g, 81.0 mmol) were suspended in NN-dimethylformamide (60 mL) and heated at 120 C for 18 h. The reaction mixture was cooled to room temperature and partitioned between water and EtOAc. The aqueous phase was washed with EtOAc (x 2) and the combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo affording the title compound as a solid (2.5 g). The aqueous phase was concentrated in vacuo and the slurry was extracted with EtOAc. The volatiles were removed in vacuo and the resulting residue was purified via flash chromatography on silica gel (solvent gradient: 0%-100% EtOAc in cyclohexane) and then triturated with cyclohexane affording a second batch of 2-(4-methoxypiperidin-l -yl)pyrimidin-4-amine (2.38 g, 87% combined yield). LCMS (ESI): [M+H]+ = 209.2; lH NMR (400 MHz, CDC13) delta: 7.94 (1H, d, J=5.60 Hz), 5.74 (1H, d, J=5.60 Hz), 4.53 (2H s), 4.33-4.24 (2H, m), 3.47-3.37 (4H, m), 3.33-3.24 (2H, m), 1.98-1.87 (2H, m), 1.60-1.47 (2H, 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. 7461-50-9, 2-Chloropyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; DIEDERICH, Francois; DOTSON, Jennafer; HANAN, Emily; HEFFRON, Timothy; LAINCHBURY, Michael; HEALD, Robert; SEWARD, Eileen M.; WO2014/210354; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

13479-88-4, 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. 13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, 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 0 C solution of 5,7-dichlorothiazolo[5,4-d]pyrimidine 4 (950 mg, 4.6 mmol) in acetonitrile (20 mL) was added benzylamine (593 mg, 5.5 mmol). The reaction mixture was stirred at the room temperature for 16 hours and then refluxed for 2 hours. The resulting mixture was cooled down and concentrated under reduced pressure, the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate= 3: 1) to give the compound 5 (950 mg, 74%) as brown oil. 1H NMR (300 MHz, CDC13): delta 8.66 (s, 1H), 7 ‘.52-7 ‘.27 (m, 5H), 6.63 (br, 1H), 4.80 (s, 2H).

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. 13479-88-4, 5,7-Dichlorothiazolo[5,4-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ZHOU, Han-Jie; PARLATI, Francesco; WUSTROW, David; WO2014/15291; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia