Tag: M.W:100-200

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.347418-42-2, name is 4-Chloro-5-fluoropyrimidine, molecular formula is C4H2ClFN2, molecular weight is 132.52, as common compound, the synthetic route is as follows.Application In Synthesis of 4-Chloro-5-fluoropyrimidine

1) Pyridinium chlorochromate,Sodium ferrate,Phosphoric acid and tetrabutylammonium chloride are added to the water,Pass argon as a protective gas,Then heated to 120 C as reactant A;Dissolving 4-chloro-5-fluoropyrimidine in DMSO as reactant B;Maintain 120 C and protective gas conditions,Passing reactant A to drop B into A,Control the dropping time to 60min,After the completion of the dropwise addition, the system was further heated to 140 C.The reaction was completed at 4.5 h.The ratio of each material in the reaction is 4-chloro-5-fluoropyrimidine,Chlorination reagent,Ferrate,The ratio of acid to quaternary ammonium salt is 1:1.04:1.16:0.009:0.014;4-chloro-5-fluoropyrimidine and water,The amount ratio of disulfoxide was: 1 mmol: 2.2 ml: 1.4 ml.2) After cooling the system, the solid is removed by filtration.Then extracted with ethyl acetate,After washing and concentrating, a crude product is obtained.Decompression distillation gives a pure product,The yield was 97.5%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,347418-42-2, 4-Chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Shandong Nong Pharmaceutical Xue Institute; Jinan Kehai Co., Ltd.; Fu Hongxin; Yang Chaohui; Wang Ling; (5 pag.)CN108997222; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4983-28-2, 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.4983-28-2, name is 2-Chloro-5-hydroxypyrimidine, molecular formula is C4H3ClN2O, molecular weight is 130.53, as common compound, the synthetic route is as follows.

Example 9 Synthesis of 2-chloro-5-benzyloxy-pyrimidine Compound 31 Referring to the reaction scheme of , potassium carbonate (11.6 g, 84.3 mmol) was added to 10 g of the alcohol 40 (76.6 mmol) in 500 mL of MeOH, followed by benzyl bromide (10.1 mL, 84.3 mmol). After 14 hrs stirring at r.t., the reaction was stopped by addition of water (300 mL). MeOH was evaporated and the remaining aqueous layer was extracted with CHCl3. The combined CHCl3 layers were washed with brine, dried over magnesium sulfate, and filtered. Removal of the solvent followed by silica gel chromatography using 100:1 CHCl3:MeOH as eluent gave 15 g (89%) of 2-amino-5-benzyloxy-pyrimidine (31) as a white solid. 1H NMR (CDCl3) delta 8.27 (s, 2H), 7.37-7.30 (m, 5H), 5.09 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 4983-28-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; KADOR, PETER F.; US2014/235858; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4270-27-3, 6-Chloropyrimidine-2,4(1H,3H)-dione, 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, Recommanded Product: 6-Chloropyrimidine-2,4(1H,3H)-dione, blongs to pyrimidines compound. Recommanded Product: 6-Chloropyrimidine-2,4(1H,3H)-dione

4-Dimethylamino-l-aminoindan (8.5g, 48.2 ?unol) and 6- chlorouracil (3.55g, 24.2 mmol) were dissolved in DMSO (8.5 ml) , heated to 1150C and stirred for 4h. The reaction mixture was cooled to 800C and glyme (ethylene glycol dimethylether) was added to provide a thick mixture which was further refluxed for Ih. The mixture was cooled to room temperature, and the solid collected by filtration and washed well with glyme. The white solid was treated with water (50 ml) and the suspension was refluxed for 30 min, cooled to room temperature, filtered and washed thoroughly with Et2O. A white solid (4g, 58%) was provided. The free base was converted to the HCl salt by dissolving it in EtOH (32 ml) and HCl/EtOH (28% solution, 2.5 ml) and adding Et2O (70 ml) . The salt was ; cdeltalectec TSy rl”‘tfrat&n, washealpha8 with Et2O and dried to give an off-white powder (4.8g, 58%). Mp 192-193C. 1H-NMR (free base) DMSO-d6 delta :10.24 (br epsilon, IH, CONHCO), 9.68 (br s, IH, CONHC), 7.15 (br t, IH, J = 8 Hz, Ar), 6.85 and 6.78 (two br d, 2H, Ar), 6.42 (br d, IH, J = 6 Hz , CHNH), 4.87 (br q, IH, J = 7 Hz , CHNH), 4.64 (br s, IH, CCHCO), 2.75 -2.90 (br s & br m, 8H, Me2N S- CH2CH2C), 2.45 and 1.76 (m, 2H, CHCH2); 13C (free base) DMS0-ds delta : 164.27 (CHCO), 153.70 (NHCNH), 150.72 (NHCONH), 149.80 (Me2NC), 144.03, 133.59, 127.61, 116.0, 115.39, 73.27 (CHCO), 56.64 (CHNH), 42.37 (Me2N), 33.21, 29.41; Anal, (calcd for Ci5Hi8N4O2) C 62.92, H 6.34, N 19.57. Found C 62.73, H 6.45, N 19.20; MS (CI) (iBu) m/z (286.11, M); HRMS (CI, iBu) exact mass calcd for Ci5H18N4O2 286.1429, found 286.1450. 1H-NMR (HCl salt) DMS0-d6 delta: 10.38 (br s, IH, CONHCO), 10.27 (br s, IH, CONHC), 7.64 (br d, IH, J = 8 Hz, Ar), 7.45 and 7.39 (br t & br d, 2H, Ar), 7.20 (br d, IH, J = 6 Hz, CHNH), 5.00 (br q, IH, J = 7 Hz, CHNH), 4.74 (br s, IH, CCHCO), 3.35 (br m, IH, CH2CH2C), 3.0-3.12 (br s & m, 7H, Me2N & CH2CH2C), 2.57 and 1.85 (two m, 2H, CHCH2); 13C (HCl salt) DMSO-d6 delta : 164.26 (CHCO), 154.13 (NHCNH), 150.37 (Me2NC), 145.90 (NHCONH), 140.07, 135.55, 128.65, 124.39, 119.64, 73.09 (CHCO), 56.39 (CHNH), 44.78 (Me2N), 32.87, 28.29; MS (CI) (NH3) m/z (287, MH+) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4270-27-3, 6-Chloropyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES, LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2006/20070; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 22536-65-8 ,Some common heterocyclic compound, 22536-65-8, molecular formula is C5H5ClN2O, 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.

To a solution of 2-chloro-5-methoxypyrimidine (5.0 g, 34.6 mmol, 1.0 equiv) in MeOH (100 mL) and DMF (20 mL) were added triethylamine (10.5 g, 103.8 mmol, 3.0 equiv) and Pd(dppf)Cl2 (3.8 g, 5.2 mmol, 0.15 equiv). The suspension was degassed and purged with CO several times. The mixture was stirred under CO (3 Mpa) at l20C for 72 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (eluted with PE/EtOAc = 20/1 ~ 10/1) to afford the title compound methyl 5-methoxypyrimidine-2-carboxylate as a light yellow solid (3.3 g, 57% yield). LCMS: m/z: 169.0 (M+H) +

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-65-8, its application will become more common.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2927-71-1, Adding some certain compound to certain chemical reactions, such as: 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine,molecular formula is C4HCl2FN2, 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 2927-71-1.

Step A: 2-Chloro-5-fluoropyrimidine To 2,4-dichloro-5-fluoropyrimidine (15.0 g, 89.8 mmol) is added tetrahydrofuran (100 mL) and zinc powder (17.6 g, 269 mmol). The mixture is heated to 70 0C with vigorous stirring, acetic acid (5.14 mL, 89.8 mmol) is added over Ih and the mixture is heated at reflux for an additional 5h. The mixture is diluted with dichloromethane, filtered through celite, evaporated in vacuo and purified on silica gel to give the desired product (6.00 g, 50 %).

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. 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/106705; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2434-56-2, 4,6-Diaminopyrimidine, 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, 2434-56-2, blongs to pyrimidines compound. Product Details of 2434-56-2

To a suspension of pyrimidine-4, 6-diamine (342.0 mg, 3.10 mmol) and NaHCCb (286.0 mg, 3.40 mmol) in EtOH (20 mL) was added a solution of 2-chloropropanal (0.57 M, 57 mmol) in a mixed solvent of chloroform and hexane (1/2 (v/v), 100 mL). The reaction mixture was stirred in a sealed tube at 85 C overnight, then cooled down to rt and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/20) to give the title compound as brown oil (80.0 mg, yield 17.4%).MS (ESI, pos. ion) m/z: 149.2 [M+H]+;1H NMR (400MHz, DMSO-^) d (ppm): 8.84 (s, 1H), 7.09 (s, 1H), 6.46 (s, 2H), 6.26 (s, 1H), 2.40 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2434-56-2, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); 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. 32779-36-5, name is 5-Bromo-2-chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 32779-36-5

Synthesis -Aminomethyl-5-bromopyrimidine[0083] Methylamine (2.0 M in methanol, 40 mL, 80 mmol) was added to 5-bromo-2- chloropyrimidine (5.6 g, 29.0 mmol) in a sealable reaction vessel. After allowing to vent for a few minutes, the vessel was sealed, placed behind a safety shield and heated in a 115 ¡ãC oil bath for 48 hours. Upon cooling the volatiles were removed in vacuo. The material was dissolved in CH2C12 (200 mL) and washed with 1M NaOH (40 mL). The aqueous layer was extracted further with CH2C12 (2×50 mL). The combined organics were dried over MgSC>4, filtered and concentrated yielding an off white solid (5.1 g, 93percent). LCMS (m/z):188.0/190.0 (MH ).

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, 32779-36-5, 5-Bromo-2-chloropyrimidine.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 101257-82-3, 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. 101257-82-3, name is 4-Amino-5-chloropyrimidine, molecular formula is C4H4ClN3, 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.

L. [4-(3-Chloropropylsulfanyl)-3-methylpyridin-2-ylmethyl]-(5-chloropyrimidin-4-yl)amine A solution of 2.7 g (20.85 mmol) of 4-amino-5-chloropyrimidine in 20 ml of dimethylformamide is added dropwise to a suspension of 0.75 g (18.25 mmol) of sodium hydride (60% strength in paraffin) in 5 ml of dimethylformamide. The mixture is stirred at room temperature for 20 minutes. A solution of 5 g (17.38 mmol) of 2-chloromethyl-4-(3-chloropropylsulfanyl)-3-methylpyridine in 5 ml of dimethylformamide is then added dropwise in the course of 30 minutes and the mixture is then stirred at room temperature for 4 hours. It is concentrated in a high vacuum and the residue is taken up in 150 ml of water and 100 ml of dichloromethane with vigorous stirring. The aqueous phase is extracted with 3*50 ml of dichloromethane. The organic extracts are dried over magnesium sulfate and concentrated. The residue is purified by chromatography on silica gel (eluent: toluene/ethyl acetate/methanol/conc. ammonia=6/3.5/0.5/0.05). The elude is concentrated and the residue is then digested with diethyl ether. After filtration and drying of the precipitate, 2.8 g (47%) of the title compound are obtained as a colorless solid, which is used without further purification.

According to the analysis of related databases, 101257-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BYK Gulden Lomberg Chemische Fabrik GmbH; US6395732; (2002); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4774-34-9, name is 4-Hydroxypyrimidine-5-carbonitrile, the common compound, a new synthetic route is introduced below. category: pyrimidines

EXAMPLE 76 4-(1,2,4,5-Tetrahydro-benzo[d]azepin-3-yl)-pyrimidine-5-carbonitrile In analogy to the procedure described in example 4 the 4-chloro-pyrimidine-5-carbonitrile (prepared from 4-hydroxy-5-pyrimidine-carbonitrile and phosphorus oxychloride, phosphorus pentachloride and N-ethyl-N,N-diisopropylamine in acetonitril at reflux) was treated with 2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride [J. Heterocycl. Chem. (1971), 8(5), 779-83] in N,N-dimethylformamide in the presence of N-ethyl-N,N-diisopropylamine at room temperature to yield the 4-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-pyrimidine-5-carbonitrile as off white solid; MS: [M+H]+=251; m.p. 148-150 C.

The synthetic route of 4774-34-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US6218385; (2001); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 56-06-4, Adding some certain compound to certain chemical reactions, such as: 56-06-4, name is 2,6-Diaminopyrimidin-4(1H)-one,molecular formula is C4H6N4O, 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 56-06-4.

Preparation 4: 2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidine- 5-carbonitrile 2,4-Diamino-6-hydroxypyrimidine (3.00 g, 24 mmol) was added to a solution of sodium acetate (6.4g, 76 mmol) in millipore water (90 mL) and stirred at 50 C for 1 hour. While still at 50 C a solution of crude chloro(formyl)acetonitrile (3.00 g,32 mmol) in mQ water (44 mL) was added dropwise with a dropping funnel, during which time the reaction turned beigeand heating continued for 18 h at 50 C, after which time the reaction was heated to 100 C for 3 h. The reaction mixture was allowed to cool to room temperature and the solid removed by filtration. The solid was suspended in EtOH and SM aqueous KOH solution was added until the soliddissolved. Charcoal was added to the solution and the mixture stirred for 30 minutes before removal of the solid by filtration. The pH of the filtrate was adjusted to pH=6 with concentrated aqueous HCI solution during which time a precipitate formed and was collected by filtration. In order to remove the final traces of water from the solid it was dissolved in a mixture of toluene/methanol 1/1 and thenconcentrated at reduced pressure. The resultant solid was dried over P205 to afford the desired compound (1.68 g, 9.6 mmol, 40% yield) as beige solid. Procedure based on Brooks 2012.OH (400 MHz, DMSO-d6) 0 11.98 (br s, 1H) 10.74 (br s, 1H), 7.59 (s, 1H), 6.43 (s, 2H).Oc(100 MHz, DMSO-d6) 0 158.0, 154.3, 152.1, 128.2, 116.4, 99.2, 86.0. HRMS (m/z ESI): C7H5N50 EM-H]- Found 174.0415 Requires: 174.0416.

According to the analysis of related databases, 56-06-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; KELLY, Vincent; (44 pag.)WO2016/50806; (2016); A1;,
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Pyrimidine – Wikipedia