Pyrimidines

Reference of 397308-78-0 ,Some common heterocyclic compound, 397308-78-0, molecular formula is C6H6N2O3S, 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 stirred solution of 9 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylic acid (2.5 g, 13.44 mmol, 1 eq) in 47 DMF (2.5 mL) was added 825 SOCl2 (10 mL) and the resultant mixture was heated at 100 C. for 2 h. After completion, the mixture was cooled to RT was then concentrated in vacuo to give 826 4-chloro-2-(methylthio)pyrimidine-5-carbonyl chloride (2.65 g, 83.59%) as an off-white solid. (0870) LCMS: 224 [M+1]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,397308-78-0, its application will become more common.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; KUMAR, Varun; (360 pag.)US2019/106436; (2019); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 51957-32-5, 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. 51957-32-5, name is 4-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, 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.

[0485] Procedure: To a stirred solution of compound (2-(piperidin-4-yl)ethyl)sulfamide hydrochloride (0.1 g, 0.41 mmol) in DMF (4 mL) was added 4-chloro-5-methylpyrimidine (0.058 g, 0.45 mmol) and aqueous solution of potassium carbonate (0.113 g, 0.82 mmol) and the resulting mixture was stirred at 90 C for 12 h. The progress of the reaction was monitored by TLC. Then the reaction was quenched with water (20 mL) and extracted with ethyl acetate (2 × 30 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulphate, filtered and evaporated under reduced pressure. The crude obtained was purified by combiflash purifier using ethyl acetate in n-hexane to afford N-(2-(1-(5-methylpyrimidin-4-yl)piperidin-4-yl)ethyl)sulfamide (0.012 g , 9.83 %).1HNMR (400 MHz, DMSO-d6): delta 8.44 (s, 1H), 8.09 (s, 1H), 6.42 (s, 2H), 6.39 (t, J = 6 Hz, 1 H), 3.93 (d, J = 13.2 Hz, 1H), 2.90 (q, J = 7.2 Hz, 2H), 2.80 (t, J = 12.4 Hz, 2H), 2.15 (s, 3H), 1.70 (d, J = 12.8 Hz, 2H), 1.58-1.63 (m, 1H), 1.41(q, J = 6.8 Hz, 2H), 1.11-1.21-(m, 2H). LC-MS (ES) m/z = 300.1 [M+H]+.

According to the analysis of related databases, 51957-32-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
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Pyrimidine – Wikipedia

Related Products of 874676-81-0 ,Some common heterocyclic compound, 874676-81-0, molecular formula is C4H2ClIN2, 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.

[00201] Step 1 : 5-Chloro-2-iodopyrimidine (4 g, 16.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.92 g, 1.66 mmol) were suspended in THF (83 mL). 3-Ethoxy-3-oxopropylzinc bromide (33.3 mL, 16.64 mmol) was added, and the resultant mixture was stirred at room temperature for 18 hours. The mixture was diluted with saturated ammonium chloride and water (1 : 1) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc:Hexanes) to give ethyl 3-(5-chloropyrimidin-2-yl)propanoate. MS ESI calcd for C9H12C1N202 [M + H]+ 215, found 215. ‘H NMR (500 MHz, DMSO-d6) delta 8.82 (s, 2H), 4.00 (q, J= 7.1 Hz, 2H), 3.13 (t, J = 6.9 Hz, 2H), 2.78 (t, J= 6.9 Hz, 2H), 1.1 1 (t, J = 7.1 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,874676-81-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAIDLE, Andrew, M.; ALTMAN, Michael, D.; KATTAR, Solomon, D.; CHRISTOPHER, Matthew; ELLIS, John, Michael; FISCHER, Christian; NORTHRUP, Alan, B.; CHILDERS, Kaleen Konrad; WO2013/192088; (2013); A1;,
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Electric Literature of 1722-12-9 ,Some common heterocyclic compound, 1722-12-9, molecular formula is C4H3ClN2, 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.

Synthesis of Pyrimidine-2-carbonitrile:To a stirred solution of 2-chloropyrimidine (20.0 g, 174.6 mmol) in DMSO (40 mL) were added DABCO (3.72 g, 33.17 mmol), KCN (12.48 g, 192 mmol) and dropwise addition of ¾0 (15 mL) at RT. The resulting solution was stirred at RT for 48 h. After consumption of starting material by TLC, the reaction mixture was diluted with water and extracted with EtOAc. Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was triturated with Hexane to afford pyrimidine-2-carbonitrile (12 g, 65%) as dark brown solid. 1H- NMR (DMSO-de, 400 MHz): delta 9.04 (s, 2H), 8.92 (d, 1H); LC-MS: 99.41%; 107.6 (M+2); (column; X-bridge C-18, (50×3.0 mm, 3.5mu); RT 1.14 min. 0.1% Aq TFA: ACN; 0.8 ml/min); TLC: 30% EtOAc/Hexane (Rf: 0.2)

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. 1722-12-9, 2-Chloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); A1;,
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Pyrimidine – Wikipedia

Related Products of 13877-56-0, 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.13877-56-0, name is 1H-Pyrazolo[4,3-d]pyrimidin-7-amine, molecular formula is C5H5N5, molecular weight is 135.13, as common compound, the synthetic route is as follows.

1H-Pyrazolo[4,3-d]pyrimidin-7-amine (82% pure, 2.85 g, 17.3 mmol) in N,N-dimethylformamide (40 mL) was treated with N-iodosuccinimide (3.8 g, 16.9 mmol). The mixture was heated in an 80 C. oil bath for 1.5 hours then cooled and concentrated under reduced pressure. Ethanol (20 mL) and water (10 mL) was added to the residue then stirred and cooled in an ice bath. The precipitate was collected by filtration and washed with water. The filtrate was concentrated under reduced pressure then water (20 mL) was added and the solid was again collected by filtration and washed with water. The solids thus isolated were combined and dried under high vacuum to give the desired title compound as a brown powder: 1H NMR (DMSO-d6, 400 MHz) delta13.2 (s, 1H), 8.21 (s, 1H), 7.39 (bs, 2H); RP-HPLC (Hypersil HS C18, 5 mum, 100A, 250×4.6 mm; 5%-100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 8.58 min; MS:MH+ 262.0, M-H+ 259.9

The chemical industry reduces the impact on the environment during synthesis 13877-56-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hirst, Gavin C.; Arnold, Lee D.; Burchat, Andrew; Wishart, Neil; Calderwood, David; Wada, Carol K.; Michaelides, Michael R.; Ji, Zhiqin; Muckey, Melanie; US2003/225098; (2003); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 29274-24-6, 5-Chloropyrazolo[1,5-a]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, 29274-24-6, blongs to pyrimidines compound. Application In Synthesis of 5-Chloropyrazolo[1,5-a]pyrimidine

5-Chloropyrazolo[l,5-a]pyri midine (500mg, 3.25mmol) taken up in 3ml acetonitrile and 1.5ml water. 2-isopropoxy-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (lg, 3.9m mol), Potassiu m carbonate (902mg, 6.5m mol), and Pd(dppf)Cl2:DCM (267mg, 0.325m mol) added and reaction stirred in microwave in a sealed tube at 120 C for 12 minutes. Reaction cooled filtered through celite washed through with ethyl acetate and reduced in vacuo. Reaction taken up in 1:1 ethyl acetate: hexane and filtered through a plug of celite. The filtrate was ollected, dried in vacuo to obtain 740 mg of crude product to be used as is in next step. LRMS (ESI) m/z 255 [(M+H)]+, calc’d for C14H14N4O: 254.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29274-24-6, its application will become more common.

Reference:
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; GARDYAN, Michael Walter; GREEN, Michael Green; KUMI, Godwin; ZHANG, Yulian; WO2015/35117; (2015); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 54660-78-5, 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.54660-78-5, name is 4-Chloropyrimidin-5-amine, molecular formula is C4H4ClN3, molecular weight is 129.5477, as common compound, the synthetic route is as follows.

Step 1 : To a 50mL round -bottom flask was added 20mL 1, 4-Dioxane, compound 5a (885mg, 6.83mmol, l .Oeq), compound lb (1.61g, 7.52mmol, l. leq) and DIPEA (1.32g, 10.25mmol, 1.5eq). The reaction was heated to reflux for 18h. TLC (PE: EA= 1 : 1) showed the reaction was completed. The reaction mixture was concentrated in vacuum and purified by column chromatography on silica gel eluted with PE: EA= 3 : 1- 1 : 1 to afford the title compound 5b (1.5g, HPLC: 93%, Yield: 71.4%) as an orange solid.

The chemical industry reduces the impact on the environment during synthesis 54660-78-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; LIANG, Congxin; (62 pag.)WO2018/5713; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 24415-66-5, 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.24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, molecular weight is 168.58, as common compound, the synthetic route is as follows.

Example 56[0486]5-Methyl-N- {1- [4- (trifluoromethyl) phenyl] cyclopropyl} [1, 2, 4] triazolo [1, 5-a] pyrimidin-7-amine[0487][0488]Step 1: 5-Methyl-N- {1- [4- (trifluoromethyl) phenyl] cyclopropyl} [1, 2, 4] triazolo [1, 5-a] pyrimidin-7-amine[0489][0490]To a solution of commercially available 7-chloro-5-methyl- [1, 2, 4] -triazolo [1, 5-a] pyrimidine (25 mg, 0.148 mmol) and 1- [4- (trifluoromethyl) phenyl] cyclopropanamine hydrochloride (45.5 mg, 0.178 mmol) in anhydrous NMP (0.5 mL) in a 2-5 mL microwave vial was added dropwise via syringe DIEA (0.2 mL, 1.145 mmol) and the resulting solution heated via oil bath to 120 overnight. The reaction was allowed to cool and was quenched with 1 mL of sat’ d sodium bicarbonate soln. The solution was diluted with 5 mL ethyl acetate. The organic layer was separated, the aqueous was re-extracted with 2.5 mL of ethyl acetate and the organics then combined. The organics were washed with 1 mL water, dried over sodium sulfate, filtered and the filtrate concentrated to dryness. The residue was purified by reverse phase HPLC (10-90acetonitrile in water with 0.05TFA) to afford the product as a white fluffy solid. LC-MS (+ESI) m/z 334.1HNMR(500 MHz, CD3OD) delta: 8.56 (s, 1H) , 7.62 (d, J 8.6 Hz, 2H) , 7.44 (d, J 8.6 Hz, 2H) , 6.40 (s, 1H) , 5.17 (q, J 6.8 Hz, 1H) , 2.52 (s, 3 H) , 1.71-1.66 (m, 2H) , 1.64-1.61 (m, 2H) .

Statistics shows that 24415-66-5 is playing an increasingly important role. we look forward to future research findings about 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MORRIELLO, Gregori J.; CHANG, Lehua; FOSTER, Ashley; CHEN, Yili; DWYER, Michael; GUO, Zack Zhiqiang; WANG, Ming; XU, Shimin; BO, Yingjian; FU, Jianmin; (250 pag.)WO2017/277; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 145783-15-9, 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, 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: C7H9Cl2N3S, blongs to pyrimidines compound. Formula: C7H9Cl2N3S

Example 6 Synthesis of 2-[((3aR,4S,6R,6aS)-6-[[5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl]amino]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]ethanol (Compound I) Take 250mL reaction flask 4,6-dichloro-2-(propylthio)pyrimidin-5-amine (16.1g, 68mmol), 2-[[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-yl]oxy]-1-ethanol (14.8g, 68mmol), triethylamine (68.7g, 680mmol) and n-butanol (100mL) were added at atmospheric pressure. The resulting reaction mixture was sealed and heated to 100C, reflux for 55h. Followed by cooling to 30C. The solvent was distilled off. Isopropyl acetate and water, the phases were separated. The aqueous phase was extracted with isopropyl acetate, the combined organic phases, washed. Dried over anhydrous magnesium sulfate. Filter. The solvent was distilled off, give a reddish brown oil. N-heptane was added after a beating, white solid 24.9g, yield 87.2%. HPLC purity was 99.4%.

The synthetic route of 145783-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qingdao Huanghai Pharmaceutical Co., Ltd.; Zhang, Fuli; Xu, Jianguo; Liu, Xiaohua; Gao, Yongji; He, Xiaoqing; Xu, Taizhi; Hu, Jie; (12 pag.)CN103626745; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 874-14-6, 1,3-Dimethyluracil, 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: 1,3-Dimethyluracil, blongs to pyrimidines compound. Recommanded Product: 1,3-Dimethyluracil

General procedure: An 8 mL oven-dried scintillation vial equipped with a magnetic stir bar was charged with a mixture of 4-quinolone or uracil (0.50 mmol, 1.0 equiv), disulfide or thiol (0.75 mmol, 1.5 equiv), molecular iodine (I2) (128 mg, 0.50 mmol, 1.0 equiv), K2S2O8 (1.00-1.50 mmol, 2.0-3.0 equiv), and acetonitrile (CH3CN) (1 mL). The vial was capped, and the reaction mixture was stirred at 60 or 80 C for 12-16 h. Upon completion, saturated Na2S2O3 (5 mL) and distilled deionized H2O (10 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by SiO2 column chromatography to afford the desired thioether products.

The synthetic route of 874-14-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Beukeaw, Danupat; Noikham, Medena; Yotphan, Sirilata; Tetrahedron; vol. 75; 39; (2019);,
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Pyrimidine – Wikipedia