Tag: M.W:200-300

Electric Literature of 2972-52-3, 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. 2972-52-3, name is 2,4-Dichloro-5-pyrimidinecarbonyl chloride, molecular formula is C5HCl3N2O, 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.

To a solution of 9 g (42.8 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid chloride (Manchester Organics Limited) in 60 mL of ether are added 10 mL of water and the reaction mixture is stirred vigorously at 35 C. for 1 hour. After addition of ether and separation of the phases by settling, the organic phase is dried over Na2SO4, filtered and concentrated under vacuum. 7.7 g of a colourless oil that solidifies rapidly in air, and which is used immediately in the following step, are obtained. Yield=93%.

According to the analysis of related databases, 2972-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI; US2012/277220; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
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.776-53-4, name is Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate, molecular formula is C8H11N3O2S, molecular weight is 213.2568, as common compound, the synthetic route is as follows.Computed Properties of C8H11N3O2S

(3) To a suspension of the compound (2.52 g) obtained in (2) above in chloroform (70 ml) is added manganese dioxide powder (7.56 g), which is three-fold amount compared to the starting material, and the mixture is stirred vigorously at room temperature overnight. The insoluble substances are removed by filtration, and the filtrate is concentrated in vacuo to obtain a colorless solid, which is extremely insoluble in an organic solvent. The resultant solid is recrystallized from a mixed solution of chloroform and methanol, triturated with a mixed solvent of chloroform-diisopropyl ether-hexane, washed with diisopropyl ether and hexane to give 2-methylthio-5-formyl-4-aminopyrimidine (1.75 g) as colorless powder. M.p. 186-187 C, MS (m/z): 170 (MH+). IR(nujol): 3406, 3289, 3177, 1667, 1631, 1616, 1585, 1529, 1387, 1180, 781 cm-1 .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,776-53-4, Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1364950; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1059735-34-0, 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. 1059735-34-0, name is 7-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine, molecular formula is C14H13Cl2N3, 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.

A mixture of 7-benzyl-2,4-dichloro-6,8-dihydro-5H- pyrido [3,4-d]pyrimidine (10 g, 34.0 mmol), 2-piperazin-2-ylacetonitrile (10.1 g, 51.0 mmol, 2 HC1) and DIEA (17.6 g, 136 mmol, 23.7 mL) in dioxane (100 mL) was stirred at 50 C for 2 hours. B0C2O (14.8 g, 68.0 mmol, 15.6 mL) was added and the mixture was stirred at 50 C for 2 hours. The mixture was concentrated under vacuum and the residue was diluted with ethyl acetate (500 mL). The separated organic layer was washed with water (1 chi 300 mL), brine (1 chi 200 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The residue was triturated with ethyl acetate (100 mL). The precipitate was filtered and the filtered cake was washed with ethyl acetate (50 mL) and dried under vacuum to give a gray solid. The filtrate was concentrated under vacuum. The residue was purified by column chromatography over silica gel (petroleum ether/ethyl acetate 100/1 to 1/2). The desired fractions were collected and concentrated under vacuum to give solid then combined with above solid to give tert-butyl 4-(7- benzyl-2-chloro-6,8-dihydro-5H-pyrido[3,4-Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; FISCHER, John, P.; FELL, Jay, Bradford; BLAKE, James, F.; HINKLIN, Ronald, Jay; MEJIA, Macedonio, J.; HICKEN, Erik, James; CHICARELLI, Mark, Joseph; GAUDINO, John, J.; VIGERS, Guy, P.A.; BURGESS, Laurence, E.; MARX, Matthew, Arnold; CHRISTENSEN, James, Gail; LEE, Matthew, Randolf; SAVECHENKOV, Pavel; ZECCA, Henry, J.; (529 pag.)WO2017/201161; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 32779-38-7, 2-Chloro-5-iodopyrimidine, 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, COA of Formula: C4H2ClIN2, blongs to pyrimidines compound. COA of Formula: C4H2ClIN2

b) 2,5-dichloro-N-(3-((2-chloropyrimidin-5-yl)ethynyl)-2,4-difluorophenyl)benzenesulfonamide Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.56 g) was added to a solution of 2,5-dichloro-N-(3-ethynyl-2,4-difluorophenyl)benzenesulfonamide (3.0 g), 2-chloro-5-iodopyrimidine (2.6 g), DIPEA (3.0 mL) and copper(I) iodide (79 mg) in THF (50 mL) at room temperature. The mixture was stirred under a nitrogen atmosphere at room temperature for 16 hr. The reaction mixture was filtered through celite, and the filtrate was diluted with water and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (761 mg). 1H NMR (300 MHz, DMSO-d6) delta 7.22-7.32 (1H, m), 7.42 (1H, td, J=8.9, 5.9 Hz), 7.71-7.81 (2H, m), 7.87 (1H, dd, J=2.0, 0.8 Hz), 9.03 (2H, s), 10.83 (1H, s).

The synthetic route of 32779-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 145783-15-9, 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.145783-15-9, name is 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, molecular formula is C7H9Cl2N3S, molecular weight is 238.14, as common compound, the synthetic route is as follows.

4,6-Dichloro-2-(propylthio)pyrimidin-5-amine (0.5 g, 2.1 mmol) was dissolved in methanol (2 mL) and supplemented with sec-butylamine (460.0 mg, 6.3 mmol). The reaction mixture was introduced in a sealed vessel and heated at 100C for 90 min. After concentration of the reaction mixture to dryness under vacuum, the residue was purified by silica gel column chromatography.Yield: 81%.Melting point: liquid.*H NMR (DMSO -d6) d 0.87 (t, J=7.4 Hz, 3H, NHCH(CH3)CH2C/ ,), 0.95 (t, J=7.3 Hz, 3H, SCH2CH2CH3), 1.15 (d, J=6.6 Hz, 3H, NHCH(C/ ,)CH2CH3), 1.53 (m, 2H, NHCH(CH3)CH2CH3), 1.64 (h, J=7.3 Hz, 2H, SCH2CH2CH3), 2.93 (t, J=7.2 Hz, 2H, SCH2CH2CH3), 4.01 (hept, J=6.6 Hz, 1H,NHCH(CH3)CH2CH3), 4.81 (s, 2H, NH2), 6.64 (d, J=7.5 Hz, 1H, NHCH(CH3)CH2CH3).13C NMR (DMSO -d6) d 10.5 (NHCH(CH3)CH2CH3), 13.3 (SCH2CH2CH3), 19.8 (NHCH(CH3)CH2CH3), 22.8 (SCH2CH2CH3), 28.6 (NHCH(CH3)CH2CH3), 32.1 (SCH2CH2CH3), 47.9 (NHCH(CH3)CH2CH3), 119.7 (C-5), 137.3 (C-6), 152.0 (C-4), 155.0 (C-2)

Statistics shows that 145783-15-9 is playing an increasingly important role. we look forward to future research findings about 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine.

Reference:
Patent; UNIVERSITE DE LIEGE; LANCELLOTTI, Patrizio; OURY, Cecile; PIROTTE, Bernard; (140 pag.)WO2019/158655; (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. 1146629-75-5, name is (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate. This compound has unique chemical properties. The synthetic route is as follows. name: (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate

6-(2-methyl-5-nitrophenyl)-1H-indole (1 g, 4.2 mmol) was dissolved in 1,4-dioxane solution (28 mL). (4-chloro-7H-pyrrolo[2,3-d]pyrimidine-7-yl)methyl pivalate (1.35 g, 5.04 mmol) and potassium carbonate (1.74 g, 12.6 mmol) were added, and then a nitrogen gas was injected for 5 minutes to remove the gas included in the mixture solution. Then, the reaction vessel was placed in an oil bath heated to 120 C., and Pd(OAc)2 (95 mg, 0.42 mmol) and Xantphos (365 mg, 0.63 mmol) were added and stirred for 2 hours. After the reaction was completed, it was extracted with ethyl acetate and water. The collected organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified by MPLC to obtain the target compound (3.53 g, 72%) as a yellow solid. 1H NMR (400 MHz, CDCl3-d6) delta 8.84 (s, 1H), 8.56 (s, 1H), 8.20 (d, J=2.4 Hz, 1H), 8.11 (dd, J=2.4 Hz, 8.4 Hz, 1H), 7.95 (d, J=3.6 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.51 (d, J=4.0 Hz, 1H), 7.43 (d, J=8.4 Hz, 1H), 7.21 (dd, J=1.6 Hz, 8.0 Hz, 1H), 6.87 (d, J=3.6 Hz, 1H), 6.79 (d, J=4.0 Hz, 1H), 6.28 (s, 2H), 2.42 (s, 3H), 1.17 (s, 9H)

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, 1146629-75-5, (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; SIM, Tae Bo; YOON, Ho Jong; HUR, Woo Young; NAM, Yun Ju; CHOI, Hwan Geun; (17 pag.)US2018/50036; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 36847-10-6, 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 36847-10-6, name is 4,6-Dibromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

4,6-dibromopyrimidine (300 mg) and 1-cyclopropylmethanamine (130 p1) were stirred in dioxane 1,4-dioxane (6.0 ml) for 2h at 110?C. The mixture was then concentrated under reduced pressure. The crude was solubilised in DCM and water was added. The aqueous phase was extracted two times with EtOAc. The organic phase was dried (silicone filter) andconcentrated under reduced pressure. The crude was used without further purification.LC-MS (Method 2): Rt 0.99 mm; MS (ESIpos): mlz = 228 [M+H]

According to the analysis of related databases, 36847-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
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.6693-08-9, name is 2,4,6-Trichloro-5-fluoropyrimidine, molecular formula is C4Cl3FN2, molecular weight is 201.4136, as common compound, the synthetic route is as follows.Formula: C4Cl3FN2

2,6-Dichloro-5-fluoro-Lambda/-(l-methyl-lH-imidazol-4-yl)pyrimidin-4-amine l-Methyl-4-nitro-lH-imidazole (Intermediate 5, 500 mg, 3.93 mmol) was dissolved in ethanol (6.771 mL) and Pd/C (10 wt%, Degussa, 105 mg, 0.10 mmol) was added. The reaction was subjected to 1 atm of hydrogen for 3 hours. TLC indicated that the reaction was completed, and the reaction mixture was filtered through Celite. The filtrate was cooled to 00C and TEA (1.097 mL, 7.87 mmol) and 2,4,6-trichloro-5-fluoropyrimidine (obtained via the procedure described in PCT Pub. No. WO2008/132502, 792 mg, 3.93 mmol) were added. The reaction was allowed to warm to room temperature slowly overnight. The reaction mixture was filtered providing the title compound as a yellow solid (820 mg) with 95% purity. LCMS: 263 [M+Eta]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6693-08-9, 2,4,6-Trichloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; ALMEIDA, Lynsie; CHUAQUI, Claudio, Edmundo; GUAN, Amy; IOANNIDIS, Stephanos; LAMB, Michelle; PENG, Bo; SU, Qibin; WO2010/20810; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
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.83410-16-6, name is 4-Chloro-5-iodo-2,6-dimethylpyrimidine, molecular formula is C6H6ClIN2, molecular weight is 268.48, as common compound, the synthetic route is as follows.Computed Properties of C6H6ClIN2

Step 3 4-Chloro-2,6-dimethyl-5-(1-ethoxyvinyl)pyrimidine A mixture of 4-chloro-2,6-dimethyl-5-iodopyrimidine (13.5 g, 0.050 mol), (1ethoxyvinyl)tributyltin (20.0 g, 0.055 mol), lithium chloride (6.4 g, 0.150 mol), tetrakis(triphenylphosphine)palladium(0) (1.7 g, 0.0015 mol), and dioxane (100 mL) was heated under reflux for 23 h. Additional tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.0010 mol) was added and heating was continued for 25 h. The mixture was cooled, diluted with EtOAc, and! N KF (100 mL) was added. The solids were removed by filtration through Celite and the layers were separated. The organic phase was washed with pH 7 phosphate buffer (100 mL), brine (100 mL), dried MgSO4), and concentrated. Purification by flash chromatography (twice; 5-10% EtOAc/hexane) gave 6.44 g (61%) of product as a colorless oil. 1 H NMR (CDCl3) delta1.35 (t, J=7.0 Hz, 3H), 2.49 (s, 3H), 2.65 (s, 3H), 3.91 (q, J=7.0 Hz, 3H), 4.21 (d, J=2.8 Hz, 1H), 4.52 (d, J=2.8 Hz, 1H). Anal. calcd for C10 H13 ClN2 O: C, 56.47; H, 6.16; N, 13.17; Found: C, 55.13; H, 5.97; N, 13.16.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83410-16-6, 4-Chloro-5-iodo-2,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; American Home Products Corporation; US5466692; (1995); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 941685-26-3 ,Some common heterocyclic compound, 941685-26-3, molecular formula is C12H18ClN3OSi, 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 intermediate 2 (3 g, 10.6 mmol), 1-butanol (30 mL)3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1- (triisopropylsilyl) -1H-pyrrole (4.5 g, 12.7 mmol),Water (30 mL) and potassium carbonate (3.7 g, 26.5 mmol) was stirred at 100 & lt; 0 & gt; C.Then, tetrakis (triphenylphosphine) palladium (0) (0.7 g, 0.53 mmol) was added to the solution,The mixture was stirred at 100 & lt; 0 & gt; C overnight.After cooling to room temperature,The mixture was filtered through a bed of celite,Extraction under reduced pressure,Purification by silica gel column gave Intermediate 8 (2 g, 60%),As a yellow oil;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,941685-26-3, its application will become more common.

Reference:
Patent; Hangzhou East China Pharmaceutical Group New Drug Institute Co., Ltd.; Yin Jianming; Lv Yubin; Li Bangliang; (18 pag.)CN106905322; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia