Category: 5466-43-3

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.5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, molecular formula is C7H6Cl2N2, molecular weight is 189.04, as common compound, the synthetic route is as follows.Computed Properties of C7H6Cl2N2

General procedure: A solution of compound 3 (1.7 g, 8.99 mmol), an appropriate pyrazol-3-amine (360 mg, 9.89 mmol) and triethylamine (1.88 ml, 13.49 mmol) in EtOH (25 ml) were stirred at room temperature for 48 h. Solvent was removed under reduced pressure and the residure was extracted in EtOAc. The organic layer was washed with water and dried over anhydrous sodium sulphate, filtered and concentrated to yield 4 and 5 as a solid. 4 and 5 were used without for further purification for the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5466-43-3, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Aware, Valmik; Gaikwad, Nitin; Chavan, Sambhaji; Manohar, Sonal; Bose, Julie; Khanna, Smriti; B-Rao, Chandrika; Dixit, Neeta; Singh, Kishori Sharan; Damre, Anagha; Sharma, Rajiv; Patil, Sambhaji; Roychowdhury, Abhijit; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 246 – 256;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5466-43-3, 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 5466-43-3 as follows.

A mixture of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.4 g, 2.1 mmol), N-benzyl-ethylamine (0.35 mL, 2.3 mmol) and diisopropylethylamine (0.4 mL, 2.1 mmol) in anhydrous ethanol (5 mL) was heated at a temperature in the range of 20 C. to 90 C. for 18 hours. After cooling to about 20 to 35 C., the reaction mixture was concentrated under reduced pressure. The crude residue was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a light pink liquid (0.60 g, 98% yield).1H NMR (CDCl3, 300 MHz): delta 7.44-7.08 (m, 5H), 4.80 (s, 2H), 3.62 (q, J=7.8 Hz, 2H), 3.28-2.76 (m, 4H), 2.24-2.08 (m, 2H), 1.26 (t, J=7.8 Hz, 3H).LC-MSD (ES+): (m/z) 288 [(M+H)+, 100].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144731; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5466-43-3 , The common heterocyclic compound, 5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, molecular formula is C7H6Cl2N2, 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.

3,5-Dimethylisoxazole boronic acid (0.4 g, 2.8 mmol) was added to a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.75 g, 4 mmol) in tetrahydrofuran (10 mL). The mixture was flushed with N2 before addition of palladium acetate (0.07 g, 0.28 mmol) and triphenylphosphine (0.14 g, 0.56 mmol). Thereafter, 2M aqueous sodium carbonate solution was added and the mixture was reflushed with N2. The mixture was stirred at a temperature in the range of 20 C. to 50 C. for 8 to 12 hours and then cooled to about 20 to 35 C. The mixture was diluted with water and the organic layer was separated. The aqueous layer was re-extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel) to afford the title compound as a light yellow liquid (0.52 g, 53% yield).1H NMR (CDCl3, 300 MHz): delta 3.08 (t, J=7.8 Hz, 2H), 2.83 (d, J=7.8 Hz, 2H), 2.41 (s, 3H), 2.30 (s, 3H), 2.23-2.16 (m, 2H).LC-MSD (ES+): (m/z) 250 [(M+H)+, 100].

The synthetic route of 5466-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144731; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine

Reference Example 60 (R)-1-(2-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N-methylpiperidine-3-carboxamide Diisopropylethylamine (3.7 ml, 21.2 mmol) was added into chloroform (25 ml) solution of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine (1 g, 5.29 mmol) prepared in Step 3 of Reference Example 52 and (R)-(-)-3-piperidincarboxylic acid (0.75 g, 5.82 mmol), and they were stirred at 70 C. overnight. After cooing the reaction solution to room temperature, methylamine hydrochloride (0.36 g, 5.29 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (1.1 g, 5.82 mmol) and 1-hydroxybenzotriazole hydrate (0.79 g, 5.82 mmol) were added thereto, and they were stirred at room temperature overnight. The reaction solution was diluted with dichloromethane, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was crystallized by using ethyl acetate to give the titled compound (1.1 g) as a white solid. 1H NMR (400 MHz, CDCl3) delta 6.31 (brs, 1H), 4.21 (d, 1H), 4.07 (d, 1H), 3.60 (t, 1H), 3.30 (t, 1H), 2.97 (t, 2H), 2.95-2.75 (m, 5H), 2.42 (brs, 1H), 2.15-2.00 (m, 3H), 2.00-1.90 (m, 1H), 1.80-1.70 (m, 1H), 1.55 (d, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 5466-43-3.

Reference:
Patent; YUHAN CORPORATION; SIM, Jae Young; CHA, Myung; KIM, Tae Kyun; YOON, Young Ae; KIM, Dong Hoon; (59 pag.)US2016/90374; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, molecular formula is C7H6Cl2N2, molecular weight is 189.04, as common compound, the synthetic route is as follows.category: pyrimidines

Intermediate 14; 2-Chloro-iV-( 1 -methyl- lH-imidazol-4-yl)-6,7-dihvdro-5H-cvclopentardlpyrimidin-4-amineA mixture of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine (321 mg, 1.70 mmol),DIPEA (0.89mL, 5.1 mmol) and 1 -methyl- lH-imidazol-4-amine (prepared from Intermediate 1 as described in the synthesis of Intermediate 10, 200 mg, 2.04 mmol) in EtOH (15 mL) was heated overnight at 700C. LCMS analysis indicated that the reaction was complete. The title product (350 mg) was obtained after filtration and was used in a subsequent step without any further purification.1H NMR (300 MHz, DMSO-J6) delta ppm 9.72 (s, 1 H), 7.46 (d, J=I .32 Hz, 1 H), 7.30 (d, J=I .51 Hz, 1 H), 3.67 (s, 3 H), 2.76 (m, 4 H), 2.02 (dq, J=7.72, 7.54 Hz, 2 H). LCMS: 250.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5466-43-3, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, molecular formula is C7H6Cl2N2, molecular weight is 189.04, as common compound, the synthetic route is as follows.category: pyrimidines

Intermediate 14; 2-Chloro-iV-( 1 -methyl- lH-imidazol-4-yl)-6,7-dihvdro-5H-cvclopentardlpyrimidin-4-amineA mixture of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine (321 mg, 1.70 mmol),DIPEA (0.89mL, 5.1 mmol) and 1 -methyl- lH-imidazol-4-amine (prepared from Intermediate 1 as described in the synthesis of Intermediate 10, 200 mg, 2.04 mmol) in EtOH (15 mL) was heated overnight at 700C. LCMS analysis indicated that the reaction was complete. The title product (350 mg) was obtained after filtration and was used in a subsequent step without any further purification.1H NMR (300 MHz, DMSO-J6) delta ppm 9.72 (s, 1 H), 7.46 (d, J=I .32 Hz, 1 H), 7.30 (d, J=I .51 Hz, 1 H), 3.67 (s, 3 H), 2.76 (m, 4 H), 2.02 (dq, J=7.72, 7.54 Hz, 2 H). LCMS: 250.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5466-43-3, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5466-43-3, 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 5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

[00571] To a solution of 2,4-dichloro-5H,6H,7H-cyclopenta[d]pyrimidine (3 g, 15.87 mmol) in THF (15 mL) was added 6M aq NaOH solution (10 eq, 26.45 ml) and the reaction stirred at 50 C for 48 h. The reaction mixture was concentrated in vacuo to remove the organic solvent. The resulting aqueous solution was acidified to pH 4 with 5M aq HC1 solution and extracted with EtOAc (2 x 50 ml), dried over sodium sulfate and concentrated in vacuo to afford the title compound (2.09 g, 75%) as a pale orange powder. [00572] Method B: LC-MS m/z = 170.9 [M + H]+; RT = 0.68 min.

According to the analysis of related databases, 5466-43-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QUARTET MEDICINE, INC.; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); TEBBE, Mark, Joseph; ATTON, Holly, Victoria; AVERY, Craig; BROMIDGE, Steven, Mark; KERRY, Mark; KOTEY, Adrian, Kotei; MONCK, Nathaniel, J.; MENICONI, Mirco; RIDGILL, Mark, Peter; TYE, Heather; SAIAH, Eddine; JOHNSSON, Kai, Peter; GORSKA, Katarzyna, Irena; PENG, Hairuo; MCCALL, John, Michael; (356 pag.)WO2017/59191; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5466-43-3, 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 5466-43-3 as follows.

General procedure: To the solution of compound 8 (0.23g, 1.2mmol) in THF (5mL) was added DIPEA (1.8mmol) and bicyclic amine or piperidin amine (1.44mmol). The reaction was stirred at r.t. for overnight. Then the mixture was diluted with ethyl acetate, washed with brine, dried over MgSO4, and evaporated. The residue was purified by column chromatography to give the product. 4.1.4 40 tert-butyl 4-((2-chloro-6, 7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (9)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Article; Fang, Yuanying; Xiong, Lijuan; Hu, Jianguo; Zhang, Shaokun; Xie, Saisai; Tu, Liangxing; Wan, Yang; Jin, Yi; Li, Xiang; Hu, Shaojie; Yang, Zunhua; Bioorganic Chemistry; vol. 86; (2019); p. 103 – 111;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5466-43-3, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, 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, 5466-43-3, blongs to pyrimidines compound. Quality Control of 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine

EXAMPLE 314; 5-Bromo-3-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-yl)-1,3-dihydro-indol-2-one; To a stirring mixture of NaH (480 mg, 12.0 mmol) in THF (20 mL) at 0 C. was added 5-bromooxindole (1.00 g, 4.72 mmol) in portion. Additional THF (5 mL×3) was used to make sure all the oxindole was added into the reaction flask. After stirred for 50 min, a solution of compound 313 (892 mg, 4.72 mmol) in THF (5 mL×3) was added. The reaction was continued stir for 1 h at 0 C. and 2.5 h at room temp. A saturated NH4Cl solution (50 mL) was added into the reaction and the mixture was extracted with EtOAc (50 mL×3). The combined organic extracts was washed with brine and concentrated. The residue was triturated with MeOH and dried to give 1.27 g (74%) the title Example 314. Example 314: 1H NMR (400 MHz, DMSO-d6) delta 10.83 (s, 1H), 7.43 (m, 1H), 7.27 (s, 1H), 6.87 (m, 1H), 5.11 (s, 1H), 3.02-2.76 (m, 4H), 2.13-2.03 (m, 2H); MS (m/e) 365 (M+1), 366 (M+2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Patent; Cephalon, Inc.; US2007/281949; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5466-43-3 ,Some common heterocyclic compound, 5466-43-3, molecular formula is C7H6Cl2N2, 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.

Morpholine (0.32 mL, 3.7 mmol) was added to a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.5 g, 2.65 mmol) in anhydrous ethanol (5 mL) and stirred at a temperature in the range of 65 C. to 85 C. for 10 to 16 hours. Thereafter, the mixture was concentrated under reduced pressure and the crude was diluted with anhydrous ether. After standing at a temperature in the range of 5 C. to 10 C. for 2 hours, the precipitated solid was filtered and washed with ether. The solid was recrystallized from ethyl acetate to afford the title compound as a pale yellow solid (0.54 g, 86% yield).1H NMR (CDCl3, 300 MHz): delta 4.10-3.94 (m, 4H), 3.90-3.76 (m, 4H), 3.36-3.20 (m, 2H), 3.10-2.90 (m, 2H), 2.29-2.12 (m, 2H).LC-MSD (ES+): (m/z) 240 [(M+H)+, 100].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5466-43-3, its application will become more common.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144731; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia