Month: March 2022

Synthetic Route of 923282-39-7, 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.923282-39-7, name is 7-Chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine, molecular formula is C6H5ClN4, molecular weight is 168.58, as common compound, the synthetic route is as follows.

Compound 77: 76 (0.3 g, 0.84 mmol) was added to a solution containing 9 (0.14 g, 0.84 mmol) and Hunig’s base (0.7 mL, 4.2 mmol) in DMF (5 mL). The reaction mixture was heated to 90 C. and stirred for 1 hour. The reaction mixture was cooled to room temperature. The reaction mixture was diluted with H2O and extracted the aqueous layer with EtOAc. Combined the organics, dried with MgSO4, filtered, and concentrated. The crude residue was purified by column chromatography on silica gel using 5% CH3CN in EtOAc to afford 77 (0.11 g, 31%), ES (+) MS m/e=421 (M+1).

The chemical industry reduces the impact on the environment during synthesis 923282-39-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2007/27166; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 87253-62-1 , The common heterocyclic compound, 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid, molecular formula is C8H8N4O2, 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.

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

The synthetic route of 87253-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 29458-38-6, 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. 29458-38-6, name is 6-Methoxypyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

A stirred solution of 6-methoxypyrimidine-2, 4-diol 29 (7 g, 49.30 mmol) in phosphoryl chloride (150 mL) under argon atmosphere was heated to reflux for 4 h. The reaction was monitored by TLC; after completion of the reaction, the excess phosphoryl chloride was removed in vacuo. The residue was diluted with ice-cold water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with aqueous saturated NaHC03 solution (50 mL) followed by water (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude compound 30 (3 g, 34%) as colorless oily liquid. TLC: 10% EtOAc/ hexanes (Rf. 0.7); 1H-NMR (CDC13, 500 MHz): delta 6.72 (s, 1H), 4.03 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29458-38-6, 6-Methoxypyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ARNOLD, Lee Daniel; MAAG, Hans; TURNER, JR., William W.; (274 pag.)WO2016/168619; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 52854-14-5, 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.52854-14-5, name is 4-Chloro-6-methoxy-5-nitropyrimidine, molecular formula is C5H4ClN3O3, molecular weight is 189.56, as common compound, the synthetic route is as follows.

General procedure: 4-chloro-6-methoxy-5-nitro-pyrimidine (Preparation R1a; 1.0 eq.), the appropriate phenol (1.2 eq.), and potassium carbonate (1.2 eq.) were dissolved in acetonitrile. It was stirred at 80 C till completion, then water was added to the reaction mixture. MeCN was evaporated. The residue extracted with DCM. The combined organic phase was dried over MgS04 and evaporated under reduced pressure to give R2a-R2ce.

Statistics shows that 52854-14-5 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-6-methoxy-5-nitropyrimidine.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; WEBER, Csaba; KOTSCHY, Andras; VASAS, Attila; KISS, Arpad; MOLNAR, Balazs; MACIAS, Alba; FIUMANA, Andrea; DAVIES, Nicholas; MURRAY, James Brooke; SELLIER, Emilie; DEMARLES, Didier; IVANSCHITZ, Lisa; GENESTE, Olivier; (233 pag.)WO2020/8013; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 114969-66-3, 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. 114969-66-3, name is 5-Bromo-4-cyanopyrimidine, molecular formula is C5H2BrN3, 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.

EXAMPLE 41A Ethyl 3-aminothieno[3,2-d]pyrimidine-2-carboxylate 5-Bromo-4-cyanopyrimidine (2.10 g, 11.4 mmol), prepared by the method of Yamanaka, et al., Chem. Pharm. Bull., 35:3119 (1987), was treated with 1.38 g (11.5 mmol) ethyl thioglycolate and 1.21 g (11.4 g) sodium carbonate in 36 ml of refluxing ethanol. After 3 hours, the reaction mixture was cooled to room temperature, quenched with water and concentrated. The residue was purified by column chromatography on silica gel eluding first with 4:1 then 1:1 hexanes: ethyl acetate to give 1.10 g (43%) of the title compound, mp 139-141 C. 1 H NMR (300 MHz, CDCl3) delta 1.42 (t, 3H), 4.41 (q, 2H), 6.17 (br s, 2H), 9.19 (s, 1H), 9.20 (s, 1H). MS (DCI/NH3) m/e 224 (M+H)+, 241 (M+NH4)+.

According to the analysis of related databases, 114969-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott Laboratories; US5597823; (1997); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 20924-05-4 ,Some common heterocyclic compound, 20924-05-4, molecular formula is C7H8N2O4, 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.

Example 20 N-[2-(Benzothiazole-2-sulfonylamino)-ethyl]-N-[(thymin-1-yl)-acetyl]-glycine ethyl ester To the mixture of N-[2-(benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester (1.72 g, 5 mmol), (thymin-1-yl)-acetic acid (0.92 g, 5 mmol), HOBt (0.81 g, 6 mmol), and DCC (1.24 g, 6 mmol) in DMF (15 ML) was added N,N-diisopropylethylamine (1.31 ML, 7.5 mmol) at ambient temperature.The resulting reaction mixture was stirred for 5 h at the same temperature and the solvent was removed in vacuo to 5 ML. The residue was dissolved in dichloromethane (50 ML) and the precipitate was filtered.The filtrate was washed with 1N HCl aqueous solution, saturated sodium bicarbonate solution, and brine.The organic layer was dried over magnesium sulfate and filtered.The filtrate was concentrated and the residue was triturated with ethyl alcohol.The resulting solid was filtered off and dried in vacuo to give the title compound (1.91 g, 75%) as a white solid. 1H NMR (500 MHz; DMSO-d6) delta 11.29 (s, 0.6H), 11.28(s, 0.4H), 8.99(brs, 0.6H), 8.82(brs, 0.4H), 8.28(m, 1H) 8.18(d, 1H) 7.66(m, 2H) 7.31(s, 0.6H) 7.42(s, 0.4H) 4.66(s, 1.2H) 4.47(s, 0.8H) 4.31(s, 0.8H), 4.05(s, 1.2H), 4.04(q, 1.2H), 3.55(t, 1.2H), 3.40~3.34(m, 2.8H), 3.20(t, 0.8H), 1.73(s, 3H), 1.19(t, 1.2H), 1.14(t, 1.8H).

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. 20924-05-4, 2-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kim, Sung Kee; Lee, Hyunil; Lim, Jong Chan; Choi, Hoon; Jeon, Jae Hoon; Ahn, Sang Youl; Lee, Sung Hee; Yoon, Won Jun; US2003/225252; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 25746-87-6 ,Some common heterocyclic compound, 25746-87-6, molecular formula is C7H10N2O2, 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.

Pyrimidine-4-carbaldehyde (C12) A solution of 4-(dimethoxymethyl)pyrimidine (C11) (90 g, 0.58 mol) and concentrated hydrochloric acid (10 mL) in water (300 mL) was heated at 60-70 C. for 24 hours. The mixture was cooled and evaporated under reduced pressure to afford a glass-like mass, which was basified with aqueous potassium carbonate solution and extracted with ethyl acetate. The combined organic layers were concentrated in vacuo, and the residue was purified by distillation to afford the product as an oil. Yield: 16.3 g, 0.15 mol, 26%. GCMS m/z 108.0 (M+). 1H NMR (400 MHz, DMSO-d6) delta 7.90 (dd, J=5.0, 1.5 Hz, 1H), 9.14 (d, J=5.0 Hz, 1H), 9.49 (d, J=1.5 Hz, 1H), 9.96 (s, 1H).

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. 25746-87-6, 4-Dimethoxymethylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc; US2011/98272; (2011); 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 56741-95-8, name is 2-Amino-5-bromo-4-hydroxy-6-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C10H8BrN3O

To a solution of 35 (0.25 g, 0.94 mmol) in DMF (8 mL) was added NEt3 (0.14 mL, 0.99 mmol) and diethyl pyrocarbonate (0.27 mL, 1.89 mmol). The reaction mixture was maintained at 65 C. for 20 h. The solvent was removed and the residue treated with DCM. The resulting mixture was filtered to remove the remaining starting material 35 and the filtrate washed with aqueous NaHCO3, brine and dried (MgSO4). The filtrate was concentrated and purified by HPLC (Thomson ODS-A 100A 5mu 150×21.2 mm column; flow rate=30 mL/min; CH3CN with 0.05% TFA (A), Water with 0.05% TFA (B); Make up pump flow=0.9 mL/min; Make up pump mobile phase; MeOH with 0.05% TFA using a gradient system as follows: t=0; 15% A, 85% B; t=3.0 min; 15% A, 85% B; t=9.5 min; 70% A, 30% B; t=10.0 min; 100% A, 0% B; t=12.0 min; 100% A, 0% B; t=12.5 min; 15% A, 85% B; t=15.0 min; 15% A, 85% B.) to afford 54 mgs of 36 (17%) as a clear oil: 1H NMR (400 MHz, CDCl3)delta 7.66 (m, 1H), 7.44 (m, 3H), 4.26 (q, J=7.6 Hz, 2H), 1.32 t, J=6.8 Hz, 3H); MS (+)-ES [M]+338.1 [M+2]+340.0 m/z. Elemental analysis for C13H12BrN3O3: calc’d: C, 46.17; H, 3.58; N, 12.43; found: C, 46.43; H, 3.74; N, 11.95.

With the rapid development of chemical substances, we look forward to future research findings about 56741-95-8.

Reference:
Patent; Averett, Devron R.; US2005/54590; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3551-55-1 ,Some common heterocyclic compound, 3551-55-1, molecular formula is C6H8N2O2, 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.

2,4-Dimethoxypyrimidine (1.4 g, 10 mmol) was dissolved in tetrahydrofuran (14 mL) under nitrogen. cool down to around 0 C, 1M magnesium dichloride(2,2,6,6-tetramethylpiperidine)lithium salt (11 mL, 11 mmol) was added dropwise with stirring. Stirring was continued for 2 hours, then iodine (2.79 g, 11 mmol) was added with stirring. After maintaining the low temperature reaction for 2 hours, it was naturally warmed to room temperature and stirring was continued for 6 hours. The reaction was quenched with aqueous ammonium chloride solution was poured into ethyl acetate and extracted three times were combined, washed, dried, and concentrated. After the obtained crude column chromatography, 5-iodo-2,4-dimethoxypyrimidine (2.34 g, yield: 88%) was obtained

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3551-55-1, its application will become more common.

Reference:
Patent; Fuxin Fulongbao Pharmaceutical Technology Co., Ltd.; Cai Fanping; Li Xinming; (5 pag.)CN109232385; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 19808-30-1, 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. 19808-30-1, name is 5-Bromopyrimidin-4(3H)-one, molecular formula is C4H3BrN2O, 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 mixture of 5-bromopyrimidin-4-ol (1-111) (40 g, 0.22 mol) in POCI3 (300 mL) was added in a dropwise manner DIPEA (29 g, 0.22 mol) at room temperature. Then the resulting mixture was heated to reflux for 3 hr. TLC (petroleum ether/EtOAc 1 :1) showed the reaction was complete. Excess POCI3 was removed through distillation under reduced pressure. The residue was poured into ice-water (300 mL) slowly with stirring. The mixture was extracted with EtOAc (2 x 300 mL), the combined organic layers were washed with water (300 mL), brine (300 mL), dried over Na2S04 and concentrated under vacuum. The residue was purified by silica gel chromatography (petroleum ether/EtOAc from 20:1 to 10:1) to give 5-bromo-4-chloropyrimidine (1-112) (25 g, 60%) as a yellow oil.

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 19808-30-1, 5-Bromopyrimidin-4(3H)-one.

Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia