Category: 13223-25-1

Electric Literature of 13223-25-1 ,Some common heterocyclic compound, 13223-25-1, molecular formula is C6H7ClN2O2, 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: To amine (3.0 mmol, 3.0 eq.) in i-PrOH (2.0 mL) was added NEt3(416 muL, 3.0 mmol, 3.0 eq.). To this was added 2-chloro-4,6-dimethoxypyrimidine(174 mg, 1.0 mmol, 1.0 eq.). A greased reflux condenser was attached and themixture heated to reflux (120 C). The reaction was left at this temperatureuntil deemed complete by TLC analysis, typically 6 – 12 h. The reaction wasthen allowed cool to room temperature and then diluted with either EtOAc (10mL, substrates 3 and 4) or Et2O (10 mL, all othersubstrates). This was then washed with water (5 mL). The aqueous phase was thenextracted with the appropriate solvent as previously used (EtOAc or Et2O,3 × 10 mL). The combined organic layers were then washed with brine (10 mL),dried over MgSO4 and then concentrated under reduced pressure toafford the title compound in its crude form. Purification by columnchromatography (silica gel, hexanes:EtOAc, 100:0 ? 60:40) afforded the titlecompound.

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. 13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shaw, Julian W.; Barbance, Laure; Grayson, David H.; Rozas, Isabel; Tetrahedron Letters; vol. 56; 35; (2015); p. 4990 – 4992;,
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Synthetic Route of 13223-25-1, 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 13223-25-1 as follows.

A mixture of (2R*, 4S*) -4-amino-2-ethyl-6-methoxy-3, 4-dihydro-2H- [1, 5] naphthyridine-l-carboxylic acid ethyl ester (300 mg), 2-chloro-4,6- dimethoxypyrimidin (468 mg), N, N-diisopropylethylamine (0.467 ml) and 1,4-dioxane (5 ml) is heated under reflux for 2 days. The reaction solution is concentrated under reduced pressure, and the resulting residue is purified by column chromatography (silica gel; hexane: ethyl acetate = 80 : 20-60 : 40) to give (2R*, 4S*)-4- (4, 6-dimethoxypyrimidin-2-yl) amino-2- ethyl-6-methoxy-3, 4-dihydro-2H- [1, 5] naphthyridine-1-carboxylic acid ethyl ester (280 g). MS (m/z) : 418 [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,13223-25-1, its application will become more common.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; WO2005/95395; (2005); A2;,
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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. 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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. Product Details of 13223-25-1

Reference Example 9 2-(4-Iodophenoxy)-4,6-dimethoxypyrimidine In the same manner as in Reference Example 8, 4-iodophenol (223 mg) and 2-chloro-4,6-dimethoxypyrimidine (192 mg) were reacted by using sodium hydride to obtain 2-(4-iodophenoxy)-4,6-dimethoxypyrimidine (322 mg).

With the rapid development of chemical substances, we look forward to future research findings about 13223-25-1.

Reference:
Patent; TORAY INDUSTRIES, INC.; EP1840121; (2007); A1;,
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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 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

A mixture of 2-chloro-4,6-dimethoxypyrimidine (87 mg, 0.50 mmol, 1 equiv), 2- napthylboronic acid (95 mg, 0.55 mmol, 1.1 equiv), THF (150 tL) were stirred into slurry. Then K3P045H20 (0.33 g, 1.1 mmol, 2.2 equiv) was added followed by a THF stock solution of 3 andPAd3 (10 pL, 0.025 pmo1 of Pd/PAd3). The reaction vial was capped then taken outside the glove box to an oil bath preset at 100 C for 5 h. The reaction mixture was diluted with ethyl acetate then extracted with water. The combine organic layers were evaporated and the crude product was purified by flash chromatography. After drying, 106 mg (80 %) of 10 was obtained as a white solid.?H NMR (501 MHz, CDC13) 6 8.99- 8.92 (m, 1H), 8.22 (ddt, J- 7.0, 2.7, 1.4 Hz, 1H), 7.97(ddt, J 23.5, 8.1, 1.4 Hz, 2H), 7.64-7.51 (m, 3H), 6.14 -6.09 (m, 1H), 4.11 -4.06 (m, 6H).13C{1H}{?H} NMR (126 MHz, CDC13) 6 171.3, 165.7, 135.5, 134.2, 131.1, 130.6, 129.4, 128.5,126.5, 126.3, 125.7, 125.1, 88.0, 54.2.HRMS (ESI) m/z calculated for C16H,4N202 (M+1) 267.1128, found 267.1123.

With the rapid development of chemical substances, we look forward to future research findings about 13223-25-1.

Reference:
Patent; THE TRUSTEES OF PRINCETON UNIVERSITY; CARROW, Brad P.; CHEN, Liye; (51 pag.)WO2017/75581; (2017); A1;,
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Reference of 13223-25-1 ,Some common heterocyclic compound, 13223-25-1, molecular formula is C6H7ClN2O2, 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-Chloro-4,6-dimethoxypyrimidine (50 g, 0.29 mol) was suspended in trifluoroacetic anhydride (175 ml, 1.24 mol, 4 equiv.) and the mixture was cooled in a brine-ice bath to +2 0C. Concentrated nitric acid was then added drop-wise to the stirred mixture (CARE; effervescence and exotherm) at such a rate that the exotherm did not cause the temperature of the reaction mixture to rise above +40 0C (about 45 minutes). After 1 hour the reaction was complete (as determined by TLC of an aliquot which was quenched with water and extracted with DCM; plate eluted with DCM). The resulting thick white precipitate was poured onto ice (500 g) and the aqueous solution was extracted with dichloromethane (2 x 400 ml). The combined organic layers were then washed with saturated aqueous sodium bicarbonate solution (2 x 200 ml) until the washings remained at pH 7. The solution was dried (MgSO4) and the solvent was removed under reduced pressure to give a yellow- white crystalline solid. This material was partially dissolved in warm diethyl ether (~300ml) with stirring and then cooled in an ice-bath. Filtration gave the product as a pale yellow-white crystalline solid (56 g, 88 %).; 2-Chloro-4,6-dimethoxypyrimidine (2 g, 11.5 mol) was suspended in trifluoroacetic anhydride (3.2 ml, 23 mmol, 2 eq.) and the mixture was cooled in a brine ice-bath to +2 0C. Fuming nitric acid (0.58 ml, 13.8 mmol, 1.2 eq) was then added drop-wise to the stirred mixture (exotherm) at such a rate that the exotherm did not cause the temperature of the reaction mixture to rise above +40 0C (about 1 minute). The thick precipitate was then warmed to room temperature and left overnight. After this time the reaction was complete (as determined by TLC of an EPO aliquot which was quenched with water and extracted with DCM; TLC run with DCM and visualised with uv). Water (20 ml) was added to the resulting thick white precipitate and the aqueous solution was extracted with dichloromethane (2 x 40 ml). The combined organic layers were then washed with saturated aqueous NaHCO3 solution (-20 ml) until the washings remained at pH 7, dried (MgSO4) and the solvent was removed under reduced pressure to give a white crystalline solid (2.38 g, 95 %).

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. 13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PARADIGM THERAPEUTICS LTD.; WO2007/582; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 13223-25-1 , The common heterocyclic compound, 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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.

4-(2-Bromophenyl)piperazine-1-carboxylic acid tert-butyl ester (280 mg, 0.82 mmol),4,6-Dimethylpyrimidin-2-amine (151 mg, 1.23 mmol),Sodium tert-butoxide (0.16 g, 1.16 mmol), tris(dibenzylideneacetone) dipalladium (75 mg, 0.082 mmol) and(±)-2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl (102 mg, 0.164 mmol) was added to anhydrous tolueneIn (20 mL), the reaction was heated to 120 C for 12 hours under a nitrogen atmosphere. The reaction was stopped, and the mixture was cooled to room temperature. The mixture was poured into water (100 mL), ethyl acetate (40 mL×3), and the organic phase was combined and washed with water (50 mL) and brine (50 mL) Dry and distill off the solvent under reduced pressure.The obtained crude product was subjected to column chromatography (dichloromethane:methanol (V:V)=50:1)The title compound (white solid, 274 mg, 87%)

The synthetic route of 13223-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Guo Zhengjiang; (39 pag.)CN109912514; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13223-25-1 , The common heterocyclic compound, 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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.

(a1) Preparation of 4,6-dimethoxy-2-(4-toluenesulfonyl)pyrimidine 4.38 g (25.0 mmol) of 2-chloro-4,6-dimethoxy-pyrimidine and 4.68 g (26.3 mmol) of sodium p-toluenesulfinate were heated in 25 ml of N,N-dimethylformamide to 100 C. while stirring. After 5 hours, the solvent was removed in a rotary evaporator at 60 C./20 mbar. The residue was taken up in 90 ml of water and 90 ml of ethyl acetate. After the organic phase had been separated off, the aqueous phase was again extracted with 75 ml of ethyl acetate. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1). The title product was obtained from the product fraction in the form of a white powder in a yield of 3.79 g (15 percent of theory). The melting point of the title compound was 129.2 to 133.4 C.

The synthetic route of 13223-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lonza AG; US5840892; (1998); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 13223-25-1, 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.13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, molecular weight is 174.59, as common compound, the synthetic route is as follows.

Example 7; Preparation of 2-hydroxymethyl-8-(4,6-dimethoxy-pyrimidin-2-yl)-l ,4-dioxa-8- azaspiro[4,5]decane (starting material for the preparation of Compound-7); 25 g of piperdone hydrochloride was slowly added in lots to 2g of TBAB and 67g of K2CO3 in 250 ml of acetonitrile at 50-60 (provide exact value), then 25 g of piperdone hydrochloride was slowly added in lots and the reaction mixture stirred for I hr. 29 g of 4,6-dimethoxy-2- chloropyrimidine was added slowly over a period of I hr and the reaction mixture was refluxed for 1 1 hours at 600C.The reaction mixture was neutralized with aq.NaOH solution and extracted with MDC, (methylene dichloride). Organic layer was distilled off to get l -(4-6-dimcthoy- pyrimidin-2-yl)-piperidin-4-one.45g of l -(4-6-dimethoxy-pyrimidin-2-yl)-piperidin-4-one. and 5.2 g of PTSA were stirred in toluene (400 ml) for half an hour. 21 g Glycerol ( 1.2 mole) was added drop wise and the reaction mixture was refluxed at 120 C for 7 hours. Toluene was removed to get the desired product with 85% yield.

The chemical industry reduces the impact on the environment during synthesis 13223-25-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; COUNCIL OF SCIENTIFIC &; INDUSTRIAL RESEARCH; DESHPANDE, Mukund, Vinayak; DESHPANDE, Sunita, Ranjan; SHIRAZI, Fazal; CHAUDHARY, Preeti, Madhukar; RAO, Nelavelli, Malleswara; MOHANTY, Baidyanath; SHARMA, Nageshwar, Nath; BACHHAWAT, Anand, Kumar; KALIANNAN, Ganesan; PAUL, Sanjoy; KUMAR, Raj; RAO, Bommena, Vittal; GAWALI, Bhimrao, Bodhanrao; REDDY, Vaddu, Venkata, Narayana; YADAV, Jhillu, Singh; WO2010/109299; (2010); A2;,
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Adding a certain compound to certain chemical reactions, such as: 13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, 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: 13223-25-1, blongs to pyrimidines compound. Recommanded Product: 13223-25-1

A mixture of 2-chloro-4,6-dimethoxypyrimidine (1.05 g, 6.0 mmol), (2S,6 )-2,6- dimethylmorpholine (0.78 mL, 6.3 mmol) and triethylamine (0.84 mL, 6.0 mmol) in NMP (12.0 mL) was sealed in a vial then heated at 140C under microwave irradiation for 2 h. The reaction mixture was cooled to rt, and /V-chlorosuccinimide (1.60 g, 12.0 mmol) was added and the mixture was stirred at 60C overnight. The mixture was poured into water forming a brown precipitate which was collected under vacuum filtration. The aqueous filtrate was extracted with EtOAc and combined with the solid obtained earlier. The mixture was loaded onto silica and purified by flash chromatograph (50 g KP-sil; 10-30% EtOAc in cyclohexane) afforded (2S,6 )-4-(5-chloro-4,6-dimethoxypyrimidin-2-yl)-2,6-dimethylmorpholine (916 g, 53%) as a white solid. 1H NMR (500 MHz, CDCh) d 4.47-4.43 (m, 2 H), 3.95 (s, 6 H), 3.62 (dqd, J = 10.6, 6.2, 2.5 Hz, 2 H), 2.55 (dd, J = 13.3, 10.6 Hz, 2 H), 1.25 (d, J = 6.2 Hz, 6 H); LCMS (Method T2) RT 1.62 min; m/z 288.32 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; BELLENIE, Benjamin Richard; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; HUCKVALE, Rosemary; COLLIE, Gavin; MENICONI, Mirco; BRENNAN, Alfie; LLOYD, Matthew Garth; (222 pag.)WO2019/197842; (2019); A1;,
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Reference of 13223-25-1, 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 13223-25-1 as follows.

Step 2: To an ice-cooled solution of 2-(4-nitro-1 H-pyrazol-1-yl)ethanol (1.90 g, 12.02 mmol) in THF (60 mL), NaH (673 mg, 16.82 mmol, 60 %) was added and the solution was stirred for 5 min at 0 C, then the ice bath was removed and the reaction mixture was stirred at rt for 30 min, before 2-chloro-4,6-dimethoxypyrimidine (2.31 g, 13.22 mmol) was added. After 40 min at rt, the reaction mixture was quenched with water and the org. solvent was removed in vacuo. The aq. layer was extracted with DCM (1 x), then acidified with 1 N HCI-solution to pH 2, and extracted with DCM (2x). The combined org. layers were washed with brine, dried (MgS04), filtered and the solvent removed under reduced pressure. Purification by crystallization (DCM-hept-mixture) yielded 4,6-dimethoxy-2-(2-(4-nitro-1 /-/-pyrazol-1- yl)ethoxy)pyrimidine as a beige solid. LC-MS conditions A: tR = 0.88 min, [M+H]+= 295.98.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13223-25-1, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; BOSS, Christoph; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi, T.; WO2012/110986; (2012); A1;,
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