Day: March 25, 2022

Application of 1159981-95-9 ,Some common heterocyclic compound, 1159981-95-9, molecular formula is C6H4BrN3, 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 5-bromopyrazolo[1,5-a]pyrimidine (300 mg, 1.5 mmol) in 1,4-dioxane (10 mL) and water (2 mL), were sequentially added 4-ethoxycarbonyl phenyl boronic acid (380 mg, 1.95 mmol), K3PO4 (955 mg, 4.5 mmol) and Pd(PPh3)4 (52 mg, 0.04 mmol). The reaction mixture was heated at 90 C. for 4 h under argon atmosphere then, was diluted with EtOAc and washed with water and brine solution. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, eluent petroleumether/EtOAc 9:1 to 1:1) to afford ethyl 4-(pyrazolo[1,5-a]pyrimidin-5-yl)benzoate (200 mg, 49%) of as a yellow solid. 1H NMR (400 MHz, CDCl3) delta (ppm): 8.77 (d, J=8.0, 1H), 8.18-8.15 (m, 4H), 7.33 (d, J=7.5 Hz, 2H), 7.12 (d, J=4.4 Hz, 1H), 6.77 (d, J=2.2 Hz, 1H), 4.45 (q, J=6.8 Hz, 2H), 1.44 (t, J=7.2 Hz, 3H); MS (ESI) m/z 268 [C15H13N3O2+H]+.

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. 1159981-95-9, 5-Bromopyrazolo[1,5-a]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 32998-03-1, 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 32998-03-1, name is 2,6-Dichloro-N-methylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 58; c/s-4-({4-(methylamino)-6-[(phenylmethyl)amino]-2-pyrimidinyl}amino)-lambda/-{[2- (trifluoromethy^phenyllmethyljcyclohexanecarboxamide; Step 1 : Preparation of c/’s-4-{[4-chloro-6-(methylamino)-2-pyrimidinyllamino}-lambda/-{[2- (trifluoromethvDphenyllmethyllcvclohexanecarboxamide; To a solution of 2,6-dichloro-lambda/-methyl-4-pyrimidinamine (360 mg, 2.0 mmol) and c/s-4-amino-lambda/-{[2-(trifluoromethyl)phenyl]methyl}cyclohexanecarboxamide (Intermediate 1 ) trifluoroacetate (829 mg, 2.0 mmol), in MeCN/H2O (1 :1 , 5 ml.) was added 1 N NaOH solution until a pH of 12 was achieved. The mixture was irradiated in the microwave for 4 hours at 17O0C, at which time LCMS indicated the formation of the desired product. The reaction mixture was extracted with EtOAc (2×50 ml_), washed with water (2×50 ml_), dried (Na2SO4), and concentrated to afford a waxy solid. The crude material was purified by column chromatography (Gradient from 0-5% MeOH in CH2CI2) to afford 300 mg (0.68 mmol, 34%) of a colorless wax MS (ES+) m/e 442 [M + H]+. Regiochemistry was verified by 2D NMR 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 32998-03-1, 2,6-Dichloro-N-methylpyrimidin-4-amine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/105968; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 98138-75-1, 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine, 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, name: 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. name: 6-Chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine

To a solution of 6-chloro-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine (100 mg, 0.54 mmol) in sec-BuOH (5 mL) was added (4-amino-3-methoxyphenyl)(morpholino)methanone (154 mg, 0.65 mmol) and K2C03 (150 mg, 1.08 mmol). The reaction mixture was degassed for 5 mm and then Pd2(dba)3 (30 mg, 0.032 mmol) and 2-dicyclohexylphosphino-2?,4?,6?- triisopropylbiphenyl (23 mg, 0.049 mmol) were added. The reaction flask was stirred at 110 C for 8 hr. After cooling to room temperature, the reaction mixture was filtered through a pad of celite and partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated. Purification by HPLC gave the title compound 58 mg (28% yield) as a light-brown solid. ?H NIVIR 400 MHz (DMSO-d6) 13.31 (br, 1H), 8.39 (d, J= 4 Hz, 1H), 7.98 (d, J= 8 Hz, 1H), 7.01 (m, 2H), 4.05 (s, 3H), 3.98 (s, 3H), 2.46 (m, 8H),MSm/z:385.23 [M+ 1].

The synthetic route of 98138-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael, S.; HATCHER, John; CHOI, Hwan, Geun; (198 pag.)WO2016/130920; (2016); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 354574-56-4, 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 354574-56-4, name is 4-Bromo-2,6-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: 4-(3,5-Difluoro-phenyl)-2,6-dimethyl-pyrimidine To a suspension of 8.0 g, (43 mmol) of 4-Bromo-2,6-dimethyl-pyrimidine [CAS 354574-56-4], 8.1 g (51 mmol, 1.2 equiv.) of 3,5-Difluorophenylboronic acid, an 1.917 g (33.0 mmol, 3.3 equiv.) of KF in 80 ml of DME were added 20 ml of 2M sodium carbonate solution and the mixture was purged with Argon for 10 min. Then 2.24 g (8.6 mmol, 0.2 equiv.) of Triphenylphosphine and 0.96 g (4.3 mmol, 0.1 equiv.) of Palladium acetate were added and the mixture was stirred under Argon atmosphere for 18 h at 85 C. The reaction was allowed to cool to r.t., and worked up with ethyl acetate/water. The crude material was purified by flash chromatography on silicagel (heptane/ethyl acetate 1:1) to yield the title compound (1.96 g, 21%) as a red solid, MS (ISP): m/e=221.2 (M+H)+.

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 354574-56-4, 4-Bromo-2,6-dimethylpyrimidine.

Reference:
Patent; Jaeschke, Georg; Spooren, Will; Vieira, Eric; US2007/197553; (2007); 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 149765-15-1, name is N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide. This compound has unique chemical properties. The synthetic route is as follows. name: N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide

A solution of DIAD (0.24 mL, 1.20 mmol) in anhydrous THF (1 mL) was added dropwise to amixture of 34 (180 mg, 0.74 mmol), 4a (150 mg, 0.61 mmol), and Ph3P (300 mg, 1.20 mmol)in anhydrousTHF (10 mL) at room temperature. The reaction mixture was stirred for 24 h, andit was then concentrated under reduced pressure. The crude residue was purified by columnchromatography on silica gel (gradient DCM/MeOH, 60:1, v/v; 40:1, v/v; 30:1, v/v) to give 36a(220 mg, 78%) as a colorless oil. 1H NMR (300 MHz, 0D013): 68.16 (s, 1H, NHCO), 7.29(dd,J= 0.9 Hz, 1H, H-6), 6.53 (dd, J= 3.6, 0.9 Hz, 1H, H-6), 4.74-4.31 (m, 4H, H-31 ,H-i ), 4.18-3.86 (m, 7H, H-2?, 2 x 0H20H3, PCH2), 1.36-i .27 (m, 15H, (0H3)30, 2 x 0H20H3); 130 NMR(150 MHz, 0D013): 6175.7 (NHCO), 152.3 (0-4, C-7a), 151.6 (0-2), 130.1 (0-6), 114.2 (C-4a),100.1 (0-5), 82.9 (d, 1Jc,p = 173.2 Hz, C-3 ), 79.4 (dd, 2JC,F = 19.1 Hz, 3Jc,p = 10.9 Hz, C-2 ),64.9 (d, 1Jc,p = 166.9 Hz, CH2P), 62.7, 62.6 (CH2CH3), 44.9 (d, 3JC,F = 8.5 Hz, C-i ), 40.5(C(0H3)3), 27.7 (C(CH3)3), 16.7, 16.6 (CH2CH3); 31P NMR (121 MHz, 0D013): 620.9; HRMS for019H2901FN405P [M+H] calcd.: 479.1621, found: 479.1617.

With the rapid development of chemical substances, we look forward to future research findings about 149765-15-1.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; ANDREI, Graciela; DE JONGHE, Steven; GROAZ, Elisabetta; HERDEWIJN, Piet; LUO, Min; SCHOLS, Dominique; SNOECK, Robert; (81 pag.)WO2018/55071; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 588720-12-1, 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.588720-12-1, name is Ethyl 6-bromopyrrolo[1,2-c]pyrimidine-3-carboxylate, molecular formula is C10H9BrN2O2, molecular weight is 269.09, as common compound, the synthetic route is as follows.

Example 4 (2S)-l-{[6-(2-methylbiphenyl-3-yl)pyrrolo[l,2-c]pyrimidin-3-yl]methyl}piperidine-2- To a solution of ethyl 6-bromopyrrolo[l,2-c]pyrimidine-3-carboxylate (D-L chiral chemicals, catST-KS-041: 119 mg, 0.442 mmol) in CH2CI2 (4 mL) was added diisobutylaluminum hydride in CH2CI2 (1.0 M, 440 mu, 0.44 mmol) dropwise at -78 C. The mixture was slowly warmed up to room temperature and stirred for 3 h. Then the reaction mixture was quenched with EtOAc followed by (NH4)2S04 solution then extracted with EtO Ac three times. The organic phase was combined, dried over MgS04, filtered and concentrated. The residue was purified by flash chromatography on a silica gel column eluting with 0 to 50 % EtOAc/Hexanes to give the desired product. LC-MS calculated for C8H6BrN20 (M+H)+: m/z = 225.0; found 224.9.

Statistics shows that 588720-12-1 is playing an increasingly important role. we look forward to future research findings about Ethyl 6-bromopyrrolo[1,2-c]pyrimidine-3-carboxylate.

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; SHEN, Bo; LI, Jingwei; LI, Zhenwu; LIU, Kai; ZHANG, Fenglei; YAO, Wenqing; (120 pag.)WO2017/70089; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 1398507-08-8, name is 4-((4-Amino-6-chloropyrimidin-2-yl)amino)benzonitrile, molecular formula is C11H8ClN5, 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. Application In Synthesis of 4-((4-Amino-6-chloropyrimidin-2-yl)amino)benzonitrile

Example 5 Preparation of N-[6-chloro-2-(4-cyanophenylamino)pyrimidin-4-yl]benzamide (IV) 3000 ml of acetonitrile; 150 g of 4-(4-amino-6-chloropyrimidin-2-ylamino)benzonitrile and 187 g of dimethylaminopyridine were added into a reaction vessel at 27+-3 C. and heated to 63+-2 C. under stirring. To the reaction mixture was added 425 ml of benzoyl chloride and heated to 78+-3 C. and maintained the same for 7 hrs. 50% of acetonitrile was distilled off from the reaction mixture and the reaction mixture cooled to 63+-2 C. To the reaction mixture was added 1500 ml of water, stirred for 15 mins at the same temperature and filtered. The obtained product solid was washed with water and suck dried. The wet cake was taken into an RB flask and 1500 ml of methanol was added, stirred and filtered. The obtained solid was washed with 150 ml of methanol and dried under vacuum. Dry weight: 165-175 gm.

With the rapid development of chemical substances, we look forward to future research findings about 1398507-08-8.

Reference:
Patent; Gore, Vinayak; Bharati, Choudhari; Hublikar, Mahesh; Bansode, Prakash; Sinore, Sandip; US2013/116433; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1333240-17-7, 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. 1333240-17-7, name is 2-Chloro-4,5-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.

5-Hydroxy-2-(4-trifluoromethyl-phenyI)-3H-pyrimidin-4-one (6)6To a mixture of 0.05 g (0.26 mmol) 4-trifluoromethylphenylboronic acid, 0.02 g (0.009 mmol Pd EN Cat 30, and 0.65 mL 1 M aq Cs2C03, was added a solution of 0.005 g (0.009 mmol) Iota ,Gamma- (bisdiphenylphosphino)ferrocene and 0.03 g (0.17 mmol) 2-chloro-4,5-dimethoxy-pyrirnidine in 1 mL THF, The resulting mixture was heated by microwave to 150 C for 10 minutes. After cooling, the aq layer was removed and the organic phase was filtered and concentrated, To the resulting residue was added 1 mL 33%> HBr in AcOH, and the resulting mixture was heated by microwave to 160 C for 5 min. The resulting solution was diluted with water (2 mL) and loaded onto an SCX column. After washing with MeOH (5 mL), the crude product was eluted off with 2 M ammonia in MeOH. Purification by automated mass-guided HPLC afforded 1 ,7 mg (4%) 5-hydroxy-2-(4-trifluoromethyl-phenyl)-3H- pyrimidin-4-one. ‘H NMR (499 MHz, DMSO-de ): delta 9.85 (br s, 1 H); 8.22 (d, J = 7.93 Hz, 2 H); 7.85 (d, J = 8.12 Hz, 2 H); 7.63 (br s, 1 H). High resolution mass spec (FT/ICR) calc (M+H)+ – 257.0533 found 257.0532.

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 1333240-17-7, 2-Chloro-4,5-dimethoxypyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOLKENBERG, Scott; HARRISON, Scott, T.; BARROW, James, C.; ZHAO, Zhijian; MELAMED, Jeffrey; KETT, Nathan; ZARTMAN, Amy; WO2011/109267; (2011); 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. 778574-06-4, name is 6-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 6-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Compound (C) (35.0 g, 0.106 mol) prepared in the step 2 was dissolved in 1,2-dichloroethane (850 mL), then triethylamine (14.9 mL, 0.107 mol) and 1-chloroethyl chloroformate (34.1 mL, 0.316 mol) were added thereto and the mixture was stirred under a condition of heating to reflux for 5 hours. After confirming the progress of the reaction by a thin-layer chromatography, the reaction mixture was cooled, washed with water and a saturated aqueous saline solution successively and dried over anhydrous magnesium sulfate. The resulting solution was concentrated and the residue was purified by a column chromatography (silica gel, n-hexane: ethyl acetate = 3:1). The product was dissolved in methanol (850 mL) and stirred under a condition of heating to reflux for 1 hour. After confirming the progress of the reaction by a thin-layer chromatography, it was concentrated to dryness to prepare compound (D) (23.5 g, yield: 95%).

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, 778574-06-4, 6-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1537879; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 163263-91-0, 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.163263-91-0, name is 2,4-Dichloro-6-(4-methoxyphenyl)pyrimidine, molecular formula is C11H8Cl2N2O, molecular weight is 255.1, as common compound, the synthetic route is as follows.

In a sealed tube, suspension of 1a (60 mg, 0.235 mmol) in liq. ammonia (9 ml) and ethanol (1 ml) was heated to 110 C for 4-5 h. Reaction was monitored by TLC. Solvent was distilled off under vacuum to give crude product. Crude product was purified by silica gel column chromatography using methanol/chloroform as eluent to give 1b (12 mg, 23.57%). Mp 210-212 C; 1H NMR (DMSO-d6, 300 MHz): delta 3.82 (s, 3H, OCH3), 6.20 (s, 1H, Ar), 6.55 (broad s, 2H, NH2), 6.98 (broad s, 2H, NH2), 7.04 d, 2H, J = 8.7 Hz, Ar), 7.81 (d, 2H, J = 8.7 Hz, Ar); MS (ESI+) m/z 217 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 163263-91-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; B-Rao, Chandrika; Kulkarni-Almeida, Asha; Katkar, Kamlesh V.; Khanna, Smriti; Ghosh, Usha; Keche, Ashish; Shah, Pranay; Srivastava, Ankita; Korde, Vaidehi; Nemmani, Kumar V.S.; Deshmukh, Nitin J.; Dixit, Amol; Brahma, Manoja K.; Bahirat, Umakant; Doshi, Lalit; Sharma, Rajiv; Sivaramakrishnan; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 2930 – 2939;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia