Category: 13479-88-4

Synthetic Route of 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.

Step 5N-(3-(2-Oxa-6-azaspiro[3.3]heptan-6-yl)phenyl)-5-chlorothiazolo[5,4-d]pyrimidin-7-amine Procedure:A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (108 mg, 0.526 mmol), 3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)aniline (100 mg, 0.526 mmol) and DIEA (102 mg, 0.789 mmol) in 5 mL of DMSO was stirred at room temperature for 16 hours. The mixture was poured into water and the precipitate was filtered. The crude N-(3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)phenyl)-5-chlorothiazolo[5,4-d]pyrimidin-7-amine (160 mg, 85%) was used into the next step without purification. LC-MS: 360 [M+H]+, tR=1.53 min.

According to the analysis of related databases, 13479-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13479-88-4, 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 13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Example 6. General Procedure F A mixture of the desired chlorothiazolopyrimidines i-F (1 equiv), desired aminomethyl heterocycle or benzylamine ii-F (1.1 equiv), and triethylamine (NEt3) (1.5 equiv) in 1,4-dioxane (~0.1 M) was stirred at room temperature until the reaction was complete by LC-MS and/or TLC analysis. The reaction mixture was concentrated to dryness then re-dissolved in CH2Cl2 and washed with saturated NaHCO3 solution. The organic extract was dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (typical eluents included, for example, a mixture of hexanes and EtOAc, or a mixture of CH2Cl2 and MeOH, or an 80:18:2 mixture of CH2Cl2/CH3OH/concentrated NH4OH) to afford the desired product iii-F. The product structures prepared according to General Procedure F were confirmed by 1H NMR and/or by mass analysis.

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 13479-88-4, 5,7-Dichlorothiazolo[5,4-d]pyrimidine.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; UNITED STATES DEPARTMENT OF HEALTH AND HUMAN SERVICES; SLAUGENHAUPT, Susan, A.; JOHNSON, Graham; PAQUETTE, William, D.; ZHANG, Wei; MARUGAN, Juan; (306 pag.)WO2016/115434; (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.13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, molecular weight is 206.0525, as common compound, the synthetic route is as follows.Computed Properties of C5HCl2N3S

A 10 mL round-bottom flask, was charged withcompound 45.3 (500 mg, 2.27 mmol, 1.00 equiv) and acetic acid-d4 (5 mL). The reaction was stirred for 24 hours at 110 C. The solids were filtered out and solvents were removed under reduced pressure to provide 450 mg (89%) of intermediate 58.1 as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13479-88-4, 5,7-Dichlorothiazolo[5,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13479-88-4 , The common heterocyclic compound, 13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, 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.

[00492] (+/-)-trans-Methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (284 mg, 1.55 mmol)and 5,7-dichlorothiazolo[5,4-d]pyrimidine (352 mg, 1.71 mmol) were dissolved in DMF (5 mL), then potassium carbonate (428 mg, 3.10 mmol) was added. The mixture was stirred at rt overnight. The reaction was stopped, and to the reaction mixture was added water (50 mL). The resulting mixture was extracted with ethyl acetate (50 mL x 2). The combined organic layers were washed with saturated brine (80 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to remove the solvent and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 10/1) to give the title compound as a yellow solid (317 mg, 58%).MS (ESI, pos.ion) m/z: 353.0 [M+H]1H NMR (600 MHz, CDC13) (ppm): 8.75 (s, 1H), 6.49 (d, J = 4.7 Hz, 1H), 4.63 (s, 1H), 3.76 (s, 3H), 2.50 (d, J= 5.6 Hz, 1H), 2.01 (d, J= 1.8 Hz, 1H), 1.95 (d, J= 2.5 Hz, 1H), 1.88- 1.76 (m, 2H), 1.73- 1.53 (m, 6H).

The synthetic route of 13479-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 13479-88-4, 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.13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, molecular weight is 206.0525, as common compound, the synthetic route is as follows.

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

The chemical industry reduces the impact on the environment during synthesis 13479-88-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 13479-88-4, 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 13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (300 mg, 1.46 mmol), 4-(1H- pyrazol-4-yl)aniline (233, 1.46 mmol), and iPr2NEt (0.51 mL, 2.93 mmol) in DIVIF (2.9 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (470 mg, 98%). MS (ES+) m/e 329 (M+H).

According to the analysis of related databases, 13479-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; POYUROVSKY, Masha; BARSOTTI, Anthony; KIM, Ji-In; LIU, Kevin; MORRIS, Koi; (143 pag.)WO2016/210331; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 13479-88-4, 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 13479-88-4 as follows.

Step 1 5-Chloro-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amine Procedure: A solution of 5,7-dichlorothiazolo[5,4-d]pyrimidine (300 mg, 1.45 mmol), 5,6-dimethoxypyridin-2-amine (269 mg, 1.74 mmol) and DIEA (281 mg, 2.17 mmol) in 5 mL of DMSO was stirred at room temperature for 24 hours. Then the mixture was poured into 30 mL of water, and the formed solid was filtered and washed with water. The obtained crude product was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate) to give 5-chloro-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amine (344 mg, 73%) as an off-white solid. LC-MS: 324.1 [M+H]+, tR=1.69 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13479-88-4, its application will become more common.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13479-88-4 ,Some common heterocyclic compound, 13479-88-4, molecular formula is C5HCl2N3S, 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.

[00229] To a solution of 5,7-dichloro-[l,3]thiazolo[5,4-d]pyrimidine (980 mg, 4.76 mmol) in THF (20 mL) at 0 C was added benzyl alcohol (495 ul, 4.76 mmol) and sodium hydride (114 mg, 4.76 mmol, 60% in mineral oil) and stirred at r.t. for 22 h. To the reaction mixture was added water (20ml) and extracted with EtOAc (2 x 50 ml). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification by chromatography on Si02 (gradient 100:0 – 90: 10, Heptane-EtOAc) afforded the title compound (708 mg, 47%) as a white powder. [00230] Method A: LC-MS m/z = 277.85 [M + H]+; RT = 1.39 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13479-88-4, its application will become more common.

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

13479-88-4 ,Some common heterocyclic compound, 13479-88-4, molecular formula is C5HCl2N3S, 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.

Step 1 5-Chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine Procedure: To a stirred solution of 5,7-dichlorothiazolo[5,4-d]pyrimidine (200 mg, 0.97 mmol) and 3,4,5-trimethoxybenzenamine (230 mg, 1.25 mmol) in 7 mL of DMSO was added DIEA (188 mg, 1.45 mmol) in one portion at room temperature. Then the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into 40 mL of water, and the solid obtained was filtered, washed with water (10 mL) to give a crude product. It was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate) to give 5-chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (337 mg, 98.6%) as a yellow solid. LC-MS: 353.0 [M+H]+, 726.9 [2M+H]+, tR=1.56 min.

According to the analysis of related databases, 13479-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); 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