Pyrimidines

Reference of 163622-50-2 , The common heterocyclic compound, 163622-50-2, name is 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H5IN4, 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.

Dissolve 3-iodo-4-amino-1H-pyrrole [3,4-d] pyrimidine (294 mg, 1.13 mmol) in 2 mL (1: 3) of a mixed solvent of ethanol and DME, and then add 0.25 mL of saturated sodium carbonate Solution andN-methyl 2-azaindole-3-boronic acid pinacol ester (413 mg, 1.6 mmol). After the whole system was ventilated three times, tetrakis (triphenylphosphine) palladium (127 mg, 0.11 mmol) was added to the mixture, and then the whole system was heated to 90 C. under nitrogen and stirred for 12 hours. After the reaction was completed, filtration was performed with celite, and the obtained filtrate was washed three times with water and dichloromethane. The organic phase was subjected to rotary evaporation under reduced pressure to obtain a solid, which was separated by silica gel column chromatography (eluent was dichloromethane containing 1-2% methanol), and finally 234 mg (0.88 mmol) of the target compound was obtained as a pale green solid. Yield: 78%.

The synthetic route of 163622-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yaoya Science And Technology (Shanghai) Co., Ltd.; Liang Yonghong; Zeng Zhaosen; Ling Yuan; (35 pag.)CN110452243; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 22536-65-8 ,Some common heterocyclic compound, 22536-65-8, molecular formula is C5H5ClN2O, 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 2-chloro-5-methoxypyrimidine (5.0 g, 34.6 mmol, 1.0 equiv) in MeOH (100 mL) and DMF (20 mL) were added triethylamine (10.5 g, 103.8 mmol, 3.0 equiv) and Pd(dppf)Cl2 (3.8 g, 5.2 mmol, 0.15 equiv). The suspension was degassed and purged with CO several times. The mixture was stirred under CO (3 Mpa) at l20C for 72 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (eluted with PE/EtOAc = 20/1 ~ 10/1) to afford the title compound methyl 5-methoxypyrimidine-2-carboxylate as a light yellow solid (3.3 g, 57% yield). LCMS: m/z: 169.0 (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,22536-65-8, its application will become more common.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4270-27-3, 6-Chloropyrimidine-2,4(1H,3H)-dione, 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: 6-Chloropyrimidine-2,4(1H,3H)-dione, blongs to pyrimidines compound. Recommanded Product: 6-Chloropyrimidine-2,4(1H,3H)-dione

4-Dimethylamino-l-aminoindan (8.5g, 48.2 ?unol) and 6- chlorouracil (3.55g, 24.2 mmol) were dissolved in DMSO (8.5 ml) , heated to 1150C and stirred for 4h. The reaction mixture was cooled to 800C and glyme (ethylene glycol dimethylether) was added to provide a thick mixture which was further refluxed for Ih. The mixture was cooled to room temperature, and the solid collected by filtration and washed well with glyme. The white solid was treated with water (50 ml) and the suspension was refluxed for 30 min, cooled to room temperature, filtered and washed thoroughly with Et2O. A white solid (4g, 58%) was provided. The free base was converted to the HCl salt by dissolving it in EtOH (32 ml) and HCl/EtOH (28% solution, 2.5 ml) and adding Et2O (70 ml) . The salt was ; cdeltalectec TSy rl”‘tfrat&n, washealpha8 with Et2O and dried to give an off-white powder (4.8g, 58%). Mp 192-193C. 1H-NMR (free base) DMSO-d6 delta :10.24 (br epsilon, IH, CONHCO), 9.68 (br s, IH, CONHC), 7.15 (br t, IH, J = 8 Hz, Ar), 6.85 and 6.78 (two br d, 2H, Ar), 6.42 (br d, IH, J = 6 Hz , CHNH), 4.87 (br q, IH, J = 7 Hz , CHNH), 4.64 (br s, IH, CCHCO), 2.75 -2.90 (br s & br m, 8H, Me2N S- CH2CH2C), 2.45 and 1.76 (m, 2H, CHCH2); 13C (free base) DMS0-ds delta : 164.27 (CHCO), 153.70 (NHCNH), 150.72 (NHCONH), 149.80 (Me2NC), 144.03, 133.59, 127.61, 116.0, 115.39, 73.27 (CHCO), 56.64 (CHNH), 42.37 (Me2N), 33.21, 29.41; Anal, (calcd for Ci5Hi8N4O2) C 62.92, H 6.34, N 19.57. Found C 62.73, H 6.45, N 19.20; MS (CI) (iBu) m/z (286.11, M); HRMS (CI, iBu) exact mass calcd for Ci5H18N4O2 286.1429, found 286.1450. 1H-NMR (HCl salt) DMS0-d6 delta: 10.38 (br s, IH, CONHCO), 10.27 (br s, IH, CONHC), 7.64 (br d, IH, J = 8 Hz, Ar), 7.45 and 7.39 (br t & br d, 2H, Ar), 7.20 (br d, IH, J = 6 Hz, CHNH), 5.00 (br q, IH, J = 7 Hz, CHNH), 4.74 (br s, IH, CCHCO), 3.35 (br m, IH, CH2CH2C), 3.0-3.12 (br s & m, 7H, Me2N & CH2CH2C), 2.57 and 1.85 (two m, 2H, CHCH2); 13C (HCl salt) DMSO-d6 delta : 164.26 (CHCO), 154.13 (NHCNH), 150.37 (Me2NC), 145.90 (NHCONH), 140.07, 135.55, 128.65, 124.39, 119.64, 73.09 (CHCO), 56.39 (CHNH), 44.78 (Me2N), 32.87, 28.29; MS (CI) (NH3) m/z (287, MH+) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4270-27-3, 6-Chloropyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES, LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2006/20070; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4983-28-2, 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.4983-28-2, name is 2-Chloro-5-hydroxypyrimidine, molecular formula is C4H3ClN2O, molecular weight is 130.53, as common compound, the synthetic route is as follows.

Example 9 Synthesis of 2-chloro-5-benzyloxy-pyrimidine Compound 31 Referring to the reaction scheme of , potassium carbonate (11.6 g, 84.3 mmol) was added to 10 g of the alcohol 40 (76.6 mmol) in 500 mL of MeOH, followed by benzyl bromide (10.1 mL, 84.3 mmol). After 14 hrs stirring at r.t., the reaction was stopped by addition of water (300 mL). MeOH was evaporated and the remaining aqueous layer was extracted with CHCl3. The combined CHCl3 layers were washed with brine, dried over magnesium sulfate, and filtered. Removal of the solvent followed by silica gel chromatography using 100:1 CHCl3:MeOH as eluent gave 15 g (89%) of 2-amino-5-benzyloxy-pyrimidine (31) as a white solid. 1H NMR (CDCl3) delta 8.27 (s, 2H), 7.37-7.30 (m, 5H), 5.09 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 4983-28-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; KADOR, PETER F.; US2014/235858; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1032452-86-0 ,Some common heterocyclic compound, 1032452-86-0, molecular formula is C13H10ClN3, 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.

In 80 mL of sec-butanol, 2.44 g (10.04 mmol) of compound 2, 2.60 g (15.06 mmol) of p-toluenesulfonic acid and 2.48 g (10.04 mmol) of 4-bromo-5-nitro 2-methoxyaniline were added. The mixture was reacted at 90 C for 20 hours, detected by TLC, and the reaction was completed.It cooled to room temperature, concentrated to give a black solid, which was successively washed with acetonitrile and methyl tert-butyl ether to give 2.58 g (5.68 mmol) of Compound 3 The crude yield of 56.56 %

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1032452-86-0, its application will become more common.

Reference:
Patent; Beijing Xuanyi Pharmaceutical Technology Co., Ltd.; Jilin Huikang Pharmaceutical Co., Ltd.; Song Yuntao; A .J.buliqi; (90 pag.)CN104761544; (2019); B;,
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.347418-42-2, name is 4-Chloro-5-fluoropyrimidine, molecular formula is C4H2ClFN2, molecular weight is 132.52, as common compound, the synthetic route is as follows.Application In Synthesis of 4-Chloro-5-fluoropyrimidine

1) Pyridinium chlorochromate,Sodium ferrate,Phosphoric acid and tetrabutylammonium chloride are added to the water,Pass argon as a protective gas,Then heated to 120 C as reactant A;Dissolving 4-chloro-5-fluoropyrimidine in DMSO as reactant B;Maintain 120 C and protective gas conditions,Passing reactant A to drop B into A,Control the dropping time to 60min,After the completion of the dropwise addition, the system was further heated to 140 C.The reaction was completed at 4.5 h.The ratio of each material in the reaction is 4-chloro-5-fluoropyrimidine,Chlorination reagent,Ferrate,The ratio of acid to quaternary ammonium salt is 1:1.04:1.16:0.009:0.014;4-chloro-5-fluoropyrimidine and water,The amount ratio of disulfoxide was: 1 mmol: 2.2 ml: 1.4 ml.2) After cooling the system, the solid is removed by filtration.Then extracted with ethyl acetate,After washing and concentrating, a crude product is obtained.Decompression distillation gives a pure product,The yield was 97.5%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,347418-42-2, 4-Chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Shandong Nong Pharmaceutical Xue Institute; Jinan Kehai Co., Ltd.; Fu Hongxin; Yang Chaohui; Wang Ling; (5 pag.)CN108997222; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[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, Application In Synthesis of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Example 191[0651]2-(Fluoromethyl) -N- { (1R) -1- [3-fluoro-4- (trifluoromethyl) phenyl] -2,2-dimethylpropyl} -5-methyl [1, 2, 4] triazolo [1, 5-a] pyrimidin-7-amine[0652][0653](R) -1- [3-Fluoro-4- (trifluoromethyl) phenyl] -2, 2-dimethylpropan-1-amine hydrochloride (28.5 mg, 0.100 mmol) was added to a mixture of 7-chloro-2- (fluoromethyl) -5-methyl- [1, 2, 4] triazolo [1, 5-a] pyrimidine (20.0 mg, 0.100 mmol) in NMP (1.5 mL) . This was followed by the addition of DIEA (64.4 mg, 88 uL, 0.499 mmol) . The reaction mixture was stirred at 80 for 16 h. The resulting mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethyl acetate (3 x 15 mL) . The combined organic layers were washed with water (3 x 10 mL) , brine (3 x 10 mL) , dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by Prep-HPLC with the following conditions: Instrument, GILSON (GX-281) Column: Xbridge RP18, 5 um, 19 x 150 mm mobile phase: water (0.05NH4HCO3) and acetonitrile (40acetonitrile up to 55in 10 min, hold 100for 2 min, down to 40in 2 min) Detector, UV 220 and 254 nm. The title compound was obtainedas a solid. MS (+ESI) m/z 414.3.1HNMR(300 MHz, CD3OD) delta: 7.69-7.64 (m, 1H) , 7.52-7.44 (m, 2H) , 6.22 (s, 1H) , 5.64 (s, 1H) , 5.49 (s, 1H) , 4.76 (s, 1H) , 2.42 (s, 3H) , 1.08 (s, 9H) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 211244-81-4, 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 211244-81-4, name is 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (1.00 g, 5.18 mmol) in anhydrous dimethylformamide (25 mL) was added N-bromosuccinimide (0.99 g, 5.59 mmol) portionwise at room temperature, and the reaction mixture was stirred for 18 h. The mixture was concentrated, and the solid was triturated with hot water (1 x 20 mL), filtered, and washed with isopropanol to give title compound as a pale yellow solid (0.68 g, 2.50 mmol, 48%). ESMS m/z 272 (M+H)+; 1H NuMR (400 MHz, DMSO-J6) delta ppm 12.88 (br. S., 1 H), 8.84 (s, 1 H), 8.47 (s, 1 H), 2.57 (s, 3H).

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 211244-81-4, 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio G.; VOLLRATH, Benedikt; WADE, Warren; WO2010/71846; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C16H11ClN2

Under an argon gas atmosphere, the intermediate body 1-4 (1.6 g, 3.9 mmol), the intermediate body 1-1 (1.0 g, 3.9 mmol), tris(dibenzylideneacetone)dipalladium (0.071 g, 0.078 mmol), tri-t-butylphosphonium tetrafluoroborate (0.091 g, 0.31 mmol), sodium t-butoxide (0.53g, 5.5 mmol), and anhydrous toluene (20 mL) were sequentially mixed, and heated to reflux for 8 hours. After the reaction solution was cooled down to the room temperature, an organic layer was removed and an organic solvent was distilled away under reduced pressure. The obtained residue was refined by silica-gel column chromatography, whereby a compound 1 (2.4 g, a yield of 95%) was obtained. FD-MS analysis consequently showed that m/e was equal to 638 while a calculated molecular weight was 638.

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, 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2415769; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 330786-24-8, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below.

Step 1 To a solution of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (300 mg, 1.0 mmole), triphenylphosphine (1.04 g, 3.96 mmole) and tert-butyl (2-hydroxyethyl)carbamate (238 mg, 1.5 mmoles) in THF (25 mL) was added DIAD (0.4 mL, 2 mmoles). The reaction was stirred for 5 hrs at room temperature and then water (30 mL) was added and extracted with ethyl acetate. The organic layers were combined, washed with aq. NaHCO3 and brine, then dried (Na2SO4), filtered and concentrated. The resulting tert-butyl (2-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)carbamate was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Principia Biopharma Inc.; Goldstein, David Michael; US8673925; (2014); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia