Pyrimidines

Application of 6320-15-6 ,Some common heterocyclic compound, 6320-15-6, 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.

Preparatory Example 74 4, 6-Dimethoxy-3- (perfluoroethyl) -1H-pyrazolo [3, 4-d] pyrimidine (Scheme 13) Step 1. 1- (4-Chloro-2, 6-dimethoxypyrimidin-5-yl) -2, 2, 3, 3, 3-pentafluoropropan-1-oneTo a stirred solution of 4-chloro-2, 6-dimethoxypyrimidine (0.50 g, 2.86 mmol) in THF (30 mL) at -30under N2was added 2, 2, 6, 6-tetramethylpiperidinylmagnesium chloride lithium chloride complex (1.5 M in THF, 1.4 mL, 2.86 mmol) dropwise. The reaction solution was stirred at -30for 2 h whereupon a copper (I) cyanide di (lithium chloride) complex solution (1 M in THF, 2.86 mL, 2.86 mmol) was added dropwise. The reaction mixture was stirred for an additional 30 min at -30whereupon 2, 2, 3, 3, 3-pentafluoropropanoic anhydride (1.78 g, 5.7 mmol) was added. The reaction mixture allowed to gradually warm to RT and was stirred for 16 h. The resulting mixture was quenched with sat. aq. sodium bicarbonate (50 mL) , diluted with water (50 mL) and extracted with EtOAc (3 x 50 mL) . The combined organic layers were washed with brine (1 x 30 mL) , dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-10ethyl acetate in hexanes) to afford the title compound as an oil.1H NMR (400 MHz, CDCl3) delta: 4.11 (s, 3H) , 4.10 (s, 3H) .

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. 6320-15-6, 4-Chloro-2,6-dimethoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO. LTD.; SHEN, Dong-Ming; DWYER, Michael; SINZ, Christopher J.; WANG, Deping; STACHEL, Shawn; PAONE, Daniel; NOMLAND, Ashley; BERGER, Richard; CHEN, Yili; QIAN, Yimin; XU, Shimin; HU, Chunmei; (212 pag.)WO2016/192083; (2016); A1;,
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Related Products of 89284-85-5 , The common heterocyclic compound, 89284-85-5, name is Methyl 2,5,6-trichloropyrimidine-4-carboxylate, molecular formula is C6H3Cl3N2O2, 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.

A mixture of I (1.5 g, 6.2 mmol) and (rac) 3-hydroxymethylmorpholine (875 mg, 7.4 mmol) with DIPEA ( 1.6 ml_, 9.3 mmol) in EtOH (30 mL) was heated at 75C for 1 h 30 min. The mixture was cooled down to rt and solvents were removed in vacuo. The oily residue was redisolved in DCM (20 mL), washed with sat. solution of NaHC03 (3 x 20 mL), brine (30 mL), dried over Na2S04 and concentrated in vacuo. Required product, intermediate II (1.860 g, 93%) was used further without additional purifications.

The synthetic route of 89284-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUNDACION CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS CARLOS III; PASTOR FERNANDEZ, Joaquin; FERNANDEZ-CAPETILLO RUIZ, Oscar; MARTINEZ GONZALEZ, Sonia; BLANCO APARICIO, Carmen; RICO FERREIRA, Maria del Rosario; TOLEDO LAZARO, Luis Ignacio; RODRIGUEZ ARISTEGUI, Sonsoles; MURGA COSTA, Matilde; VARELA BUSTO, Carmen; LOPEZ CONTRERAS, Andres Joaquin; RENNER, Oliver; NIETO SOLER, Maria; CEBRIAN MUNOZ, David Alvaro; WO2014/140644; (2014); A1;,
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Related Products of 63200-54-4 , The common heterocyclic compound, 63200-54-4, name is 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H3Cl2N3, 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.

Into a 50 ml_ vial was placed 2,4-dichloro-5H-pyrrolo[3,2-c/]pyrimidine [CAS 63200-54-4] (1 g, 5.319 mmol), DMF (10 ml_), DIPEA (2.75 ml_, 16 mmol) and benzyl bromide (0.7 ml_, 5.85 mmol). The vial was sealed and shaken for 16 hours at room temperature. The solvents were removed under reduced pressure. The crude was purified via silica gel column chromatography using a heptane to ethyl acetate gradient. The best fractions were pooled and the solvents were removed under reduced pressure to afford B. LC-MS (M+H) m/z = 278

The synthetic route of 63200-54-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; MC GOWAN, David Craig; LAST, Stefaan Julien; PIETERS, Serge Maria Aloysius; EMBRECHTS, Werner; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; WO2014/56953; (2014); A1;,
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Related Products of 444731-75-3, 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. 444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, molecular formula is C14H14ClN5, 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.

Procedure 5 To a stirred suspension of the product of Intermediate Example 4 (1.0 g, 3.6 mmol) in 10 mL of CH3CN, was added 5-amino-2- methylbenzenesulfonamide (0.70 g, 3.8 mmol, I.Oequiv) at room temperature. The reaction mixture was heated at reflux for 3 h, then 4 M HCI in 1,4-dioxane (18 (at)L, 0.076 mmol) was added in one portion. After 20 h, the suspension was cooled to room temperature, and filtered. The resulting solid was washed with 10 mL of CH3CN and dried in the air to yield 1.3 g (73%) of 5-((at)4-[(2,3-dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl}amino)-2- methyl benzenesulfonamide monohydrochloride as an off-white solid.

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 444731-75-3, N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; KUMAR, Rakesh; WO2005/105094; (2005); A2;,
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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 34289-60-6, name is 4,6-Dimethylpyrimidin-2-ol hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4,6-Dimethylpyrimidin-2-ol hydrochloride

Add 160 mg (1 mmol) to a 100 mL eggplant bottle 2-hydroxy-4,6-dimethylpyrimidine hydrochloride, 318 mg (3 mmol) benzaldehyde and 0.1 mL (1.2 mmol) concentrated hydrochloric acid,Anhydrous ethanol (40 mL) was added to dissolve the reaction, and the mixture was heated under reflux at 80 C for 24h.After the reaction is completed, the solvent is distilled off under reduced pressure.Add a saturated sodium bicarbonate aqueous solution and stir to remove the acid.The crude product was washed with water and dried and purified by column chromatography (methanol: dichloromethane = 1:10).0.21 g of 2-hydroxy-4,6-distyrylpyrimidine was obtained in a yield of 70%.

With the rapid development of chemical substances, we look forward to future research findings about 34289-60-6.

Reference:
Patent; Ocean University of China; Jiang Tao; Zhang Lijuan; Tong Sheng; Zhang Meng; (30 pag.)CN105198820; (2019); B;,
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Application of 5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

After adding a solvent N-methylpyrrolidone 12L to a 20 L double-layer glass reactor, the mechanical stirrer was turned on to stir.Then the substrate 2-(isopropylsulfonyl)aniline (199.3 g, 1 mol) was added sequentially.Potassium tert-butoxide (168.3 g, 1.5 mol),2,4,5-trichloropyrimidine (238.5 g, 1.3 mol),Zinc acetate (55.0 g, 0.3 mol),After stirring and dispersing uniformly, the temperature is raised to 120±2 C. for the heat preservation reaction;After 10 h, the reaction solution was taken for HPLC analysis (area normalization method: substrate 2-(isopropylsulfonyl)aniline was 1.18%, product 98.72%,The remaining amount is unknown impurity),The reaction was continued for 2 hours, and the reaction solution was subjected to HPLC analysis (area normalization method: substrate 2-(isopropylsulfonyl)aniline was 0.14%,99.52% of the product, the balance is unknown impurities);[0055] Stop the reaction, cool to 20-30 C and transfer to a 50L reactor;Add 8 L of isopropyl acetate under stirring, then add 30% V acetic acid aqueous solution to adjust the pH of the system to 7.5-7.8, stir 10-20pieta; – add 5.0L of purified water, stir for 8-lOmin, then let stand for 20-30 min. The liquid layer was collected, and the upper layer of isopropyl acetate was collected. The lower aqueous phase was extracted twice with isopropyl acetate, and 6.0 L of isopropyl acetate layer was added each time; all the isopropyl acetate layers were combined and washed with 10 L of saturated brine. After standing for liquid separation, the isopropyl acetate layer was collected, and then heated to 40-45 C, and 12 L of n-heptane was added dropwise with stirring, and a white solid precipitated in the system during the dropwise addition.After the addition, the temperature is lowered to 10-20 C.Then, the temperature is raised to 50-60 C, the temperature is kept 10-20pieta, and then naturally cooled to room temperature, filtered, and the filter cake is collected and dried under reduced pressure at 40-45 C to obtain 318.1 g of an off-white solid, the yield is 92.1%;The purity of 2,5-dichloro-N-[2-(isopropylsulfonyl)phenyl]pyrimidin-4-amine in white solid was 99.88%, and the unreacted substrate 2-(isopropylsulfonate) was detected by HPLC. Acyl) aniline 0.04%, the balance is unknown impurities

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 5750-76-5, 2,4,5-Trichloropyrimidine.

Reference:
Patent; Liu Gengxi; Chen Lanhua; Ji Hui; Li Jing; Liang Li; (8 pag.)CN109020898; (2018); A;,
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Pyrimidine – Wikipedia

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.2435-50-9, name is Pyrimidine-4-carbaldehyde, molecular formula is C5H4N2O, molecular weight is 108.0981, as common compound, the synthetic route is as follows.Formula: C5H4N2O

To a solu tion of e thyl (S)-2-((S)-pyrrolidine-2- carboxamido)-9-(5,6,7,8-tetrahydro-l,8-naphthyridin-2-yl)nonanoate (50 mg, 0.08 mmol, 1 equiv) in 0.5 mL MeOH was added pyrimidine-4-carbaldehyde (0.018 mL, 0.19 mol, 2.5 equiv). The mixture was heated at 40 C for 10 min before adding sodium cyanoborohydride (12 mg, 0.19 mmol, 2 5 equiv) and continuing to heat for an additional 2 h. The crude mixture was used directly in the next step

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2435-50-9, Pyrimidine-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; PLIANT THERAPEUTICS, INC.; LEFTHERIS, Katerina; REILLY, Maureen; FINKELSTEIN, Darren; COOPER, Nicole; BAILEY, Christopher; CHA, Jacob; (0 pag.)WO2020/6315; (2020); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1780-33-2, 4,6-Dichloro-2,5-dimethylpyrimidine, 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, SDS of cas: 1780-33-2, blongs to pyrimidines compound. SDS of cas: 1780-33-2

Two solutions, one with the aryl halide (0.56 mmol, 1.0 equivalent) in THF- H2O (2.5 mL, 3:2 v/v) and one with phenol (0.84 mmol, 1.5 equivalent) and NaOH (0.84 mmol, 1.5 equivalent) in THF-H2O (2.5 mL, 3:2 v/v) were prepared and then introduced into Asia microfluidic reactor by Pump A & B (see, e.g., Figure 4). The mixture was pumped through a preheated 1 mL glass microfluidic reactor at a predetermined flow rate to achieve the desired residence time. The crude product was collected in a flask and extracted with ethyl acetate. The organic phase was combined, dried MgSO4 and concentrated under reduced pressure. The isolated crude product was purified using a prepacked silica cartridge on a Teledyne CombiFlash Rf 200 instrument. Fractions corresponding to the product peak were combined and concentrated using rotavap to afford 1 as white solid (135 mg, 87percent).1H NMR (CDC13) delta2.08 (s, 3H), 2.36 (s, 3H), 2.41 (s, 3H), 3.79 (s, 3H), 6.72- 6.79 (m, 2H) and 6.94 (d, J= 8.4 Hz, 1H); 13C NMR (CDC13) delta11.6, 16.7, 25.5, 55.6, 111.9, 113.0, 116.2, 122.6, 131.3, 144.9, 157.1, 160.1, 165.2 and 168.1; mass spectrum (APCI), m/z calcd for C14H16C1N202 (M+H)+ 279.0895, found 279.0888.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-33-2, 4,6-Dichloro-2,5-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; ALAM, Mohammad Parvez; JOHN, Varghese; JOGODZINSKA, Barabara; (120 pag.)WO2018/48953; (2018); A1;,
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Pyrimidine – Wikipedia

Reference of 42754-96-1, 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.42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2Cl2N4, molecular weight is 189, as common compound, the synthetic route is as follows.

Intermediate 70; 4,6-Dichloro-l-(tetrahvdro-2H-pyran-2-yl)-lH-pyrazolor3,4-dlpyrimidine 103496-1PTo a solution of 4,6-dichloro-lH-pyrazolo[3,4-d]pyrimidine (Intermediate 71, 2 g, 10.58 mmol) and/?-Ts-OEta (0.201 g, 1.06 mmol) in DCM (30 mL) and THF (30.0 mL), was added 3,4- dihydro-2H-pyran (1.335 g, 15.87 mmol). The resulting solution was stirred overnight at ambient temperature whereupon the volatiles were removed under reduced pressure. The residue left, was dissolved in DCM and the organic layer was washed with saturated aqueous sodium carbonate

The chemical industry reduces the impact on the environment during synthesis 42754-96-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 16075-42-6, 2-Amino-4-(trifluoromethyl)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: 2-Amino-4-(trifluoromethyl)pyrimidine, blongs to pyrimidines compound. name: 2-Amino-4-(trifluoromethyl)pyrimidine

To a solution of 2-amino-4-trifluoromethylpyrimidine (25 g, 0.15 mol) in CH3CN (600 mL) was added in the dark a solution of N-bromosuccinimide (34.8 g, 195 mmol) in acetonitrile (200 mL) over a period of 2.5 h. The reaction mixture was stirred for 4.5 h at RT and then concentrated. The residue was dissolved in EtOAc and H2O, the organic solvents were separated, washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography using EtOAc in hexane from 10% to 40% to provide the title compound as a beige solid (31.2 g, 85%). LC-MS: Rt 0.82 min; (LCMS method 2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16075-42-6, 2-Amino-4-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; Fairhurst, Robin Alec; Furet, Pascal; Kalthoff, Frank Stephan; Lerchner, Andreas; Rueeger, Heinrich; US2014/135330; (2014); A1;,
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Pyrimidine – Wikipedia