Pyrimidines

Synthetic Route of 3001-72-7, 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 3001-72-7, name is 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

N-methyl-1,5-diazabicyclo[4.3.0]non-5-enium dimethyl phosphate ([mDBN][Me2PO4]) was prepared using a Syrris glass-jacketed reactor. For a 250g batch of [mDBN][Me2PO4] the following method was used: 116.89ml (0.946mol) of DBN was charged to the reactor followed by flushing the headspace with argon gas. 110.71ml (0.946mol) of trimethyl phosphate was added to the DBN at 60C under argon atmosphere, as to keep the temperature below 80C during the exothermic reaction. The mixture was then heated to 75C where it was kept for one hour and then cooled to room temperature. The product was an oil-like yellow liquid (Fig. 1).

According to the analysis of related databases, 3001-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Parviainen, Helena; Parviainen, Arno; Virtanen, Tommi; Kilpelaeinen, Ilkka; Ahvenainen, Patrik; Serimaa, Ritva; Groenqvist, Stina; Maloney, Thaddeus; Maunu, Sirkka Liisa; Carbohydrate Polymers; vol. 113; (2014); p. 67 – 76;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 94741-69-2, 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.94741-69-2, name is 4-Amino-2-chloro-5-pyrimidinecarbonitrile, molecular formula is C5H3ClN4, molecular weight is 154.56, as common compound, the synthetic route is as follows.

Step 5A: (2R)-4-(4-arnino-5-cvanopyrirnidin-2-yl)-N-[2-(l-benzylpiperidin-4- yl)ethyll-2-methylpiperazine-l -carboxamide (0311) To a solution of (2R)-N-[2-(l-benzylpiperidin-4-yl)ethyl]-2- methy lpiperazine- 1 -carboxamide 4a (0.20 g, 0.58 mmol, 1.0 eq) and 4-amino-2- chloropyrimidine-5-carbonitrile (0.90 g, 0.58 mmol, 1.0 eq) in NMP (2 mL) was added N,N-diisopropylethylamine (0.38 mL, 2.3 mmol, 4.0 eq) and the reaction mixture heated to 100 C for 1 hr. In some cases, lower temperatures or longer reaction times were used. The reaction mixture was cooled, diluted heavily with EtOAc, and washed repeatedly with brine (3x). The organic layer was dried over Na2SC>4 and concentrated. Silica gel column (24 g) was loaded using methylene chloride and run using an increasing gradient of MeOH (0-20%) in methylene chloride over 20 min to provide (2R)-4-(4-ainino-5-cyanopyrimidin-2-yl)-N-[2-(l-benzylpiperidin-4-yl)ethyl]-2- methylpiperazine-l-carboxamide 5-1 (0.14 g, 0.31 mmol, 53%) as an off-white foam.

The chemical industry reduces the impact on the environment during synthesis 94741-69-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; HARRIOTT, Nicole; PAGANO, Nicholas; (135 pag.)WO2017/79641; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 3740-92-9, name is 4,6-Dichloro-2-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C10H6Cl2N2

4,6-Dichloro-2-phenylpyrimidine (5.0 g, 22.2 mmol) and NaOCH3 (3.6 g, 66.6 mmol) was stirred in methanol (500 mL) on an ice bath for 1 h, then brought to reflux for 7 h. After evaporation, the white solid was dissolved in DCM (100 mL) and washed with water. Evaporation of the organic phase yielded 8 (3.98 g, 81%) as a white solid. 1H NMR (CD3OD): delta 8.39-8.36 (m, 2H), 7.53-7.44 (m, 3H), 6.76 (s, 1H), 4.08 (s, 3H). 13C NMR (CD3OD): delta 172.3, 165.9, 162.2, 137.4, 132.6, 129.5, 129.5, 106.0, 55.0. MS calcd for C11H9ClN2O [M+H]+ 221.0, found: 221.0.

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, 3740-92-9, 4,6-Dichloro-2-phenylpyrimidine.

Reference:
Article; Lampa, Anna; Alogheli, Hiba; Ehrenberg, Angelica E.; Akerblom, Eva; Svensson, Richard; Artursson, Per; Danielson, U. Helena; Karlen, Anders; Sandstroem, Anja; Bioorganic and Medicinal Chemistry; vol. 22; 23; (2014); p. 6595 – 6615;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine, molecular formula is C5H4Cl2N2O, 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. HPLC of Formula: C5H4Cl2N2O

Method 2 4-(5-Methoxy-4-pyrimidinyl)-2-methylpiperazine A solution of 2-methylpiperazine (20 g) in water (100 mL) was reacted with solid 4,6-dichloro-5-methoxypyrimidine (5.00 g, 27.9 mmole) in a procedure similar to that given for Method 2 of Example 14. After hydrogenation and filtration of the catalyst, the product was extracted from the filtrate with CH2 Cl2. The extracts were concentrated in vacuo, and the residue was Kegelrohr distilled to give a clear oil (5.46 g, 99.8%). The oil was dissolved in acetonitrile and concentrated HCl added to form the salt which was recrystallized from i-PrOH and dried in vacuo to give the product as a White powder (4.02 g, m.p. 185-188 C.).

With the rapid development of chemical substances, we look forward to future research findings about 5018-38-2.

Reference:
Patent; Bristol-Myers Squibb Company; US5300506; (1994); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 115093-90-8, name is 4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C6H3Cl2N3

General procedure: The 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine (0.11 mmol) was added to 3-(4- amino-i H-pyrazol -1 -yl)-N-(6-methylpyridin-3 -yl)benzamide (0.1 mmol) in tBuOH (1.0 mL) and stirred at 90 C for 12 h. The solvent was evaporated and the residue was purified by reverse-phase preparative HPLC to give the product.Procedures in Scheme 4 were utilized to synthesize this compound. LC-MS: 445(M+H).

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, 115093-90-8, 4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; FENG, Yangbo; LOGRASSO, Philip; ZHENG, Ke; PARK, Chul Min; WO2015/84936; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below., Formula: C6H4ClN3

EXAMPLE 584-{7-Fluoro-8-methyl-3-r(l»S^-l-(pyrazolori,5-alpha1pyrimidin-7-ylamino’)ethyl]quinolin-2- yl I piperazine- 1 -carboxamide Intermediate 36 (50 mg, 0.151 mmol), 7-chloropyrazolo[l,5-alpha]pyrimidine (34.7 mg, 0.226 mmol), DIPEA (0.079 mL, 0.453 mmol) and n-BuOH (1 mL) were combined and heated under microwave irradiation at 1400C for 1 h. After cooling, the mixture was dissolved in EtOAc (100 mL) and washed with saturated brine (3 x 20 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. Purification by preparative HPLC gave the title compound (7 mg, 10%) as a yellow solid. deltaH (DMSO-d6) 8.24 (d, J4.99 Hz, IH), 8.14 (s, IH), 8.10 (d, J2.33 Hz, IH), 7.70 (dd, J8.89, 6.22 Hz, IH), 7.25 (t, J9.13 Hz, IH), 6.58 (d, J7.55 Hz, IH), 6.51 (d, J2.33 Hz, IH), 6.40 (d, J 5.03 Hz, IH), 5.46 (s, 2H), 5.05 (t, J6.89 Hz, IH), 3.95-4.02 (m, 2H), 3.81-3.88 (m, 2H), 3.67-3.75 (m, 2H), 3.27-3.32 (m, 2H), 2.49 (d, J2.33 Hz, 3H), 1.29 (d, J6.59 Hz, 3H). LCMS (ES+) 449 (M+H)+, RT 2.59 minutes (Method 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, 58347-49-2, 7-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; LANGHAM, Barry, John; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2010/133836; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 90213-66-4, 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.90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3Cl2N3, molecular weight is 188.01, as common compound, the synthetic route is as follows.

After 2,4-dicWoro-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 16.0 mmol) was dissolved in acetone (20.0 mL), 4- methylbenzenesulfonyl chloride (4.6 g, 23.9 mmol) was added thereto. After cooling to 0 C, 2 M sodium hydroxide solution (12.0 mL) was slowly added dropwise and then stirred at room temperature for 2 hours. The organic layer was isolated, treated with magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was isolated by column chromatography to obtain a title compound (2.9 g, yield: 80.0%). [H NMR (500MHz,CD3OD) delta 8.12(d, 2H), 7.76(d, 1H), 7.37(d, 2H), 6.68(d, 1H), 2.43(s, 3H)

The chemical industry reduces the impact on the environment during synthesis 90213-66-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; DAEWOONG PHARMACEUTICAL CO., LTD.; KIM, In Woo; HAN, Mi Ryeong; YOO, Jakyung; OH, Yun Ju; KIM, Ji Duck; KIM, Nam Youn; JUN, Sun Ah; LEE, Jun Hee; PARK, Joon Seok; (197 pag.)WO2018/4306; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 705-24-8, 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. 705-24-8, name is 4,6-Dichloro-2-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of Intermediate IP (120 mg, 0.54 mmol) in DMF (3.0 mL) were added N,N-diisopropylethylamine (103 mu, 0.590 mmol) and 4, 6-dichloro-2- (trifluoromethyl)-pyrimidine (86 mu, 0.57 mmol). The solution was heated in a microwave at 90C for one hour, and was then partitioned between DCM and H20. The aqueous layer was extracted with DCM (2x), and the combined organic layers were washed with brine, dried Na2S04), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to afford Intermediate 12 (191 mg, 86%). LCMS (Method A): m/z 410.2 (M+H)+. XH NMR (CDC13): delta 7.66-7.52 (m, 3H), 7.27-7.25 (m, 2H), 6.35 (s, 1H), 4.94-4.86 (m, 1H), 4.12-4.07 (m, 1H), 4.01-3.95 (m, 1H), 3.61-3.52 (m, 2H), 2.99-2.83 (m, 3H), 2.64-2.55 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,705-24-8, its application will become more common.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; MCGUINNESS, Brian F; XU, Xiaoqing; KULTGEN, Steven G.; MCMASTER, Ellen Sieber; BEASLEY, James R.; (356 pag.)WO2018/5794; (2018); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 330794-31-5, 1-Cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-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, 330794-31-5, blongs to pyrimidines compound. Quality Control of 1-Cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Synthesis of 1-(3-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)ethanone (BA81, BA81d & BA81dd); A solution of tert-butyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (200 mg, 0.76 mmol) in EtOH (3.3 ml) was added to a solution of 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA80, 100 mg, 0.30 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified using silica gel column chromatography [MeOH-CH2Cl2, 5:95] yielding BA81. BA81 was dissolved in 50:50 CH2Cl2:TFA and stirred for one hour at room temperature. The reaction mixture was concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA81d. BA81d was dissolved in CH2Cl2 (2 ml) and BBr3 (4 mL, 4 mol) was added slowly with a syringe, while stirring. The reaction was stirred at room temperature for 2 hours then concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA81dd.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,330794-31-5, its application will become more common.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5751-20-2, 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. 5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below.

To a solution containing 2.0 g (14 mmol) of 2- (methylthio) pyrimidin-4(3H)-one in 10 ml of acetic acid under a nitrogen atmosphere was added 1.04 ml (14 mmol) of bromine in 2 ml acetic acid. The reaction was allowed to stir at room temperature for 30 min. The precipitated product was filtered, washed with acetic acid and suspended in hot acetic acid- To this suspention was added 0.2 ml bromine in 1ml acetic acid. The product was collected, washed with acetic acid and recrystallized from ethanol to yield 1.4 g (45 percent) of product. 1H NMR (CD30D) 5: 2. 61 (s, 3H) , 8.29 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5751-20-2, 2-(Methylthio)pyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/99688; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia