Category: 5604-46-6

Electric Literature of 5604-46-6, 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.5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, molecular formula is C5H3Cl2N3O, molecular weight is 192.0028, as common compound, the synthetic route is as follows.

A solution of methyl 1-hydrazinyl-1, 2, 3, 4-tetrahydronaphthalene-1-carboxylate hydrochloride (0.7 g, 2.7 mmol) and 2-amino-4, 6-dichloropyrimidine-5-carbaldehyde (0.52 g, 2.7 mmol) in MeCN (30 ml) was stirred at rt overnight and then heated to 70. The reaction mixture was stirred at 70 for 1h. After completion, the mixture was filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography with PE: EtOAc (5: 1) to afford product (0.66 g, 68%) as a light yellow solid. MS: M/e 358 (M+1) +.

The chemical industry reduces the impact on the environment during synthesis 5604-46-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (152 pag.)WO2019/196803; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5604-46-6, 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 5604-46-6 as follows.

Step 1: 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine To a mixture of 2-amino-4,6-dichloro-pyrimidine-5-carbaldehyde (1.0 g, 5.2 mmol) and Et3N (0.63 g, 6.2 mmol) in THF (20 mL) and H2O (2 mL) was added hydrazine H2NNH2 (10 g, 0.2 mol). Then the mixture was stirred at room temperature for 1.5 hrs. Then the mixture was concentrated in vacuo. The residue was added H2O and filtered to give 4-chloro-1H-pyrazolo[3,4-d]-pyrimidin-6-ylamine (0.8 g, yield 91%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5604-46-6, its application will become more common.

Reference:
Patent; Heald, Robert; Price, Stephen; Safina, Brian; Savy, Pascal Pierre Alexandre; Seward, Eileen Mary; Sutherlin, Daniel P.; Waszkowycz, Bohdan; US2012/202785; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5604-46-6 ,Some common heterocyclic compound, 5604-46-6, molecular formula is C5H3Cl2N3O, 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 appropriately substituted benzyl triphenylphosphonium halide (e.g., 4- chlorobenzyltriphenylphosphonium chloride, 0.66 g, 1.56 mmol), was suspended in anhydrous THF (5.0 mL) with stirring under argon and cooled to -78 0C. Then, nBuLi (0.6 mL, 2.5 M in hexane) was added dropwise over 20 minutes and stirring was continued for an additional 0.5 h. Compound 1 (0.2 g, 1.04 mmol) was suspended/partially dissolved in anhydrous THF (15.0 mL) and added dropwise to the ylide solution. The cooling bath was removed and the mixture was stirred at room temperature for 2 h whereby TLC (1 :20 THF- CH2Cl2) showed no remaining starting material, 1. The yellow solution was cooled to -78 0C and treated cautiously with ammonium chloride (satd, 15 mL). The mixture removed from the cooling bath, and stirring was continued for 1.5 h before EtOAc ( 10.0 mL) was added. The organic phase was separated, washed with water (1 x 10 mL), dried (Na2SO4), filtered, and concentrated to dryness. Flash chromatography (1 :20 THF-CH2CI2) provided compound 2a (0.1 18 g, 37.7%, mixture of cis and trans isomers) as an off-white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5604-46-6, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; SOUTHERN RESEARCH INSTITUTE; NJOROGE, F. George; PIWINSKI, John J.; SHIH, Neng-Yang; KWONG, Cecil D.; ANANTHAN, Subramaniam; CLARK, Jeremy; GENG, Feng; KEZAR, III, Hollis S.; MADDRY, Joseph A.; REYNOLDS, Robert C.; ROYCHOWDHURY, Abhijit; SECRIST, III, John A.; WO2010/22128; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5604-46-6 ,Some common heterocyclic compound, 5604-46-6, molecular formula is C5H3Cl2N3O, 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.

2. Procedures for preparation of compound 11; NH2 H NH2 N”‘N 0 H p NN H ci cl (furoic hydrazide) ci H ou compound V CH3CN compound))) Na2CO3 40 Deg. C H0- NH NH2 80 Deg. C Zu NH2 Nu2 Nf H (at) N”S compound 11 Compound V (1. 0g, 1. Oeq.), 2-furoic hydrazide (0.7g, 1. 1 eq.) and sodium carbonate (0.55g, 1. Oeq. ) were added acetonitrile (20mL) and was heated to 40C. After stirring at 40C for 30 hours, the reaction was subsequently heated to 60C. A solution of 2- hydroxyethyl hydrazine (0.7mL, 2eq. ) in water (5mL) was added. The reaction mixture was then heated to 80C and stirred for 2.5 hours. Once the reaction was completed, the reaction mixture was cooled down to 25C, and 0.1 N HCI (10mL) was added. The reaction mixture was stirred at 25C for 2 hours. The reaction mixture was then concentrated to about 1 OmL under reduced pressure. Water (30mL) was added and the reaction mixture was concentrated to about 1 OmL under reduced pressure. The reaction mixture was stirred at 25C for overnight. The solid was filtered and washed with 2mL water, then with 2mL acetonitrile. The product (compound 1) was dried under vacuum at 25C to yield 1. 1 g (70%) of the desired product. LC/MS: m/z=304 (M+1) 1H NMR (DMSO-d6) : 610. 65 (d, 1H) ; 9.52 (d, 1H) ; 7.98-7. 88 (m, 1H) ; 7.42-7. 29 (m, 1H) ; 6.73-6. 70 (m, 1H) ; 6.35 (s, 2H); 4.9 (s, 1H) ; 4.1 (m, 2H); 3.62 (m, 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. 5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; WO2005/54245; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, 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, Formula: C5H3Cl2N3O, blongs to pyrimidines compound. Formula: C5H3Cl2N3O

To a mixture of 112a (253 mg, 1.1 mmol) and 112b (192 mg, 1.0 mmol) was added DMF (20 ml) and the reaction mixture was stirred at room temperature overnight. Then poured the mixyure into ice/saturated sodium bicarbonate solution (40 ml). The precipitated solid was collected by filtration and washed with water. The solid was taken in DMF (10 ml) and added gl. acetic acid (10 drops). The reaction mixture was stirred at room temperature overnight and processed as above. The solid thus obtained (223 mg) was taken in dichloromethane (10 ml) and treated with DDQ (138 mg, 0.6 mmol) at room temperature for 1 hr. The reaction mixture was diluted with chloroform (30 ml) and washed with saturated sodium bicarbonate solution (50 ml). Separated the organic layer, and the aqueous layer was extracted with EtOAc (50 ml). Combined the organic layers, dried (Na2SO4), filtered and concentrated to provide 112c which was taken further without any purification.

The synthetic route of 5604-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; SOUTHERN RESEARCH INSTITUTE; ARASAPPAN, Ashok; NJOROGE, F., George; BENNETT, Frank; GIRIJAVALLABHAN, Vinay, M.; HUANG, Yuhua; HUELGAS, Regina; PIWINSKI, John, J.; SHIH, Neng-Yang; VERMA, Vishal; VELAZQUEZ, Francisco; VENKATRAMAN, Srikanth; KWONG, Cecil, D.; ANANTHAN, Subramaniam; CLARK, Jeremy; GENG, Feng; KEZAR, Hollis, S., III.; MADDRY, Joseph, A.; REYNOLDS, Robert, C.; ROYCHOWDHURY, Abhijit; SECRIST, John, A., III.; FOWLER, Anita, T.; WO2010/22121; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia