Category: pyrimidines

Reference of 126352-69-0, Adding some certain compound to certain chemical reactions, such as: 126352-69-0, name is 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine,molecular formula is C6H9N3, 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 126352-69-0.

To a solution of 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (3.0 g, 24.4 mmol) inTID’ (20 mL) was added NaH (60% in mineral oil, 1.5 g, 36.6 mmol). The reaction was stirred atroom temperature for 1 hr under N2. Then Boc20 (8. 0 g, 36.6 mmol) was added and the mixturewas stirred at room temperature for 16 hrs. The reaction mixture was poured into water ( 60 mL)and extracted with EA (50 mL x2). The organic layer was washed with water (50 mL) and brine(50 mL), dried over Na2S04 and concentrated. The residue was purified by silica gel column(DCM/J1eOH = 100/1) to give tert-butyl6,7-dihydropyrazolo[l,5-a]pyrimidine-4(5H)carboxylate(4.4 g, yield: 81 %) as a white solid.[0010221 1H NMR (300 lVlliz, CDCb): 8 = 7.37 (s, 1H), 6.28 (s, 1H), 4.21-4.16 (m, 2H), 3.86-3.80 (m, 2H), 2.20-2.15 (m, 2H), 1.57 (s, 9H). MS: m/z 224.4 (M+H’).

According to the analysis of related databases, 126352-69-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JECURE THERAPEUTICS, INC.; STAFFORD, Jeffrey A.; VEAL, James M.; TRZOSS, Lynnie Lin; MCBRIDE, Christopher; (411 pag.)WO2018/136890; (2018); 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. 1722-12-9, name is 2-Chloropyrimidine, molecular formula is C4H3ClN2, 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. Formula: C4H3ClN2

Methyl 5-methyl-2-pyrimidin-2-ylbenzoate (B-3)A solution of 13^2 (4.38 kg5 15.84 mol) from the previous reaction was charged in a visually clean 100 L reactor equipped with a mechanical stirrer and a thermocouple. The mixture was solvent switched to 2-MeTHF (35 L). This was followed by addition of 2- chloropyrimidine (2.18 kg, 19.01 mol) (endothermic 19 to 140C) and sodium carbonate (5.04 kg, 47.5 mol). To this stirring suspension was added water (11.67 L) (exothermic 15-240C). The thick slurry was degassed with N2 for 40 minutes after which PdCl2(dppf)-CH2Cl2 adduct (0.518 kg, 0.634 mol) was added which causes the reaction to become black. The internal temperature was set to 74 0C and aged for 16 h. An aliquot was taken for HPLC analysis and revealed near complete consumption of the starting boronate (>97% conv.). The reaction was cooled to room temperature, and 12 L of water and 24 L of MTBE were added while maintaining stirring for 10 minutes. This solution was filtered on Solka-Floc and transferred to a 100 L extractor. The flask was further rinsed with 4 L of both MTBE and water (x2) and then another 4 L of MTBE. The layers were cut and the aqueous layers were back-extracted with 21.5 L of MTBE. Assay of the organic layers showed the biaryl ester (2.76 kg, 12.09 mol, 76 % yield). The organics were reloaded into the extractor and 1.26 kg of activated carbon (Darco KB-G grade) was added and the mixture was stirred for 2 h and then filtered over Solka-FIoc. The filter cake was washed with 3 x 10 L of MTBE. Heavy metal analysis revealed 427-493 ppm of Pd and 882-934 ppm of Fe. Assay was 2.381 kg of EbI (66% overall, 86% recovery from DARCO). Data for B^: lH NMR (500MHz, CDCI3, 293K, TMS): 8.78 (d, J – 4.87 Hz, 2 H); 7.97 (d, J = 7.93 Hz, 1 H); 7.51 (s, 1 H); 7.39 (d, J = 7.99 Hz, 1 H); 7.19 (t, J = 4.88 Hz, 1 H); 3.75 (s, 3 H); 2.44 (s, 3 H).

With the rapid development of chemical substances, we look forward to future research findings about 1722-12-9.

Reference:
Patent; MERCK & CO., INC.; MERCK FROSST CANADA LTD.; WO2009/143033; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 19875-05-9, 4,6-Dichloro-2-(chloromethyl)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, COA of Formula: C5H3Cl3N2, blongs to pyrimidines compound. COA of Formula: C5H3Cl3N2

Description 128; 4, 6-Dichloro-2-iodomethylpyrimidine; A mixture of 4, 6-dichloro-2-chloromethylpyrimidine [Annales Pharmaceutici (Poznan) 12, 33-38, 1977] (3.3 g, 16.7 mmol) and sodium iodide (3.25 g, 21.7 mmol) in acetone (70 ml) was stirred at room temperature for 3 hours. The reaction mixture was concentrated to dryness. The residue was dissolved in ethyl acetate and the organic solution was washed with sodium thiosulfate solution (aq), brine, dried over sodium sulfate, filtered and concentrated to give a brown solid (4.5 g, 93 %). IH NMR (360 MHz, DMSO-d6) 4.53 (2 H, s), 7.93 (1 H, s).

The synthetic route of 19875-05-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2005/47279; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 272-50-4, Adding some certain compound to certain chemical reactions, such as: 272-50-4, name is 5H-Pyrrolo[3,2-d]pyrimidine,molecular formula is C6H5N3, 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 272-50-4.

To solution of 5H-pyrrolo[3,2-d]pyrimidine (2 g, 16.8 mmmol) in 1,2-ethanediol (40 mL) was added tert-butyl 4-oxopiperidine-1-carboxylate (6.7 g, 33.5 mmol) and KOH (3.8 g, 6.72 mmol). The mixture was stirred at 95oC for 18 h. The mixture was then diluted with ethyl acetate (30 mL) and washed with brine (50 mL × 3), dried over Na2SO4, and filtered. The filtrate was concentrated and the residue was purified by ISCO column on silica gel (from 100% DCM to DCM/MeOH = 10/1) to give tert-butyl 4-(5H- pyrrolo[3,2-d]pyrimidin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate as yellow oil. Yield: 3 g (60%); LCMS method D: Rt = 1.679 min; (M+H)+= 301.2.

According to the analysis of related databases, 272-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David A.; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen D.; SINGH, Suresh B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; (285 pag.)WO2018/53267; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 6622-92-0, 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 6622-92-0, name is 2,6-Dimethylpyrimidin-4-ol. This compound has unique chemical properties. The synthetic route is as follows.

4-Hydroxy-2,6-dimethylpyrimidine (546 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 2 ml ethanol at room temperature, charged with DABCO (48.4 mu, 1.46 mmol) and then stirred at 80 C under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for 1 h and the precipitates were separated by filtration. It was washed well with 50 % aqueous ethanol and dried under vacuum (1.52 g, 3.64 mmol, 82.8 %).

According to the analysis of related databases, 6622-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DEUTSCHES KREBSFORSCHUNGSZENTRUM (DKFZ); RUPRECHTS-KARLS-UNIVERSITAeT HEIDELBERG; BOUTROS, Michael; MASKEY, Rajendra-Prasad; KOCH, Corinna; FUCHS, Florian; STEINBRINK, Sandra; GILBERT, Daniel; WO2012/62905; (2012); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3524-87-6, 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 3524-87-6, name is 6-Methylpyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows.

PREPARATION EXAMPLE 48 Synthesis of 4-Chloro-6-methylpyrimidine 4-Hydroxy-6-methylpyrimidine (782 mg) was dissolved in phosphoryl chloride (6.6 mL), and the solution was heated under reflux for 1 hour. The reaction mixture was added dropwise to ice water, neutralized with an aqueous solution of 2 M sodium hydroxide and extracted with ethyl acetate. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound. Yield: 913 mg (theoretical amount).

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 3524-87-6, 6-Methylpyrimidin-4(3H)-one.

Reference:
Patent; Kowa Co., Ltd.; US6509329; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1195-08-0, 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.1195-08-0, name is 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde, molecular formula is C5H4N2O3, molecular weight is 140.1, as common compound, the synthetic route is as follows.

Example 8 5-{4-[2-(4-tert-Butyl-phenyl)-3H-imidazo[4,5-b]pyridin-7-yl]-piperazin-1-ylmethyl}-1H-pyrimidine-2,4-dione (9). 2-(4-tert-Butyl-phenyl)-7-piperazin-1-yl-3H-imidazo[4,5-b]pyridine (7) (50 mg, 0.15 mmol) and 5-formyluracil (21 mg, 0.15 mmol) were dissolved in NMP (4 ml) and sodium triacetoxyborohydride (64 mg, 0.30 mmol) was added. The reaction mixture was allowed to stir for 18 h under nitrogen. It was judged complete by MS, and purified by HPLC Method E to yield the title product 9 (25 mg (36%), 0.054 mmol). 1H NMR (DMSO-d6): delta 11.45 (s, 1H), 11.30 (d, J=3 Hz, 1H), 9.85(bs, 1H), 8.11 (d, J=8.3 Hz, 3H), 7.74 (d, J=6.1 Hz, 1H), 7.54 (d, J=8.3 Hz, 2H), 6.78 (s, 1H), 4.05 (s, 2H), 3.20-3.65 (m, 8H), 1.33 (s, 9H). (ESI-POS): [M+H]+=460; MS(ESI-NEG):[M-H]-=458.

Statistics shows that 1195-08-0 is playing an increasingly important role. we look forward to future research findings about 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde.

Reference:
Patent; WYETH; US2006/189617; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 98141-42-5, 4,6-Dichloro-1-methyl-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: 4,6-Dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. name: 4,6-Dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

To a stirred solution of (rac)-(2S,4R,6S,7S)-methyl 7-aminotricyclo[3.2.2.02,4]nonane-6-carboxylate (3.4 g, 17.4 mmol) in THF (150 ml) was added 4,6-dichloro-1-methyi-1Hpyrazolo[3,4-d]pyrimidine (4.24 g, 20.9 mmol) and (3.38 g, 4.52 ml, 26.1 mmol) at roomtemperature and the resulting reaction mixture solution was stirred at 60 oc for 16 h. After cooling to room temperature, the reaction mixture was poured into water (1 00 ml) andextracted with EtOAc (150 ml twice). The combined organic layers were washed with brine,dried over anhydrous Na2S04 , filtered and concentrated in vacuo to give a crude product,which was purified by silica gel flash chromatography (0-1 00% EtOAc-hexane gradient) toafford the title racemic compound (4.1 g, 65.1% yield) as a white solid. MS: 362.0 [M+Ht.

The synthetic route of 98141-42-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; TAN, Xuefei; ZBINDEN, Katrin Groebke; KUHN, Bernd; WANG, Lisha; LIU, Yongfu; WU, Jun; SHEN, Hong; SHI, Tianlai; (174 pag.)WO2017/133664; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 39268-74-1, 5-Ethoxypyrimidin-2-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, 39268-74-1, blongs to pyrimidines compound. Product Details of 39268-74-1

Process 4: Under argon atmosphere, trimethylaluminum (2 mol/L hexane solution, 0.39 mL, 0.78 mmol) was added to 1,2-dichloroethane (5 mL) solution of 2-amino-5-ethoxypyrimidine (108 mg, 0.78 mmol) at room temperature and stirred for 70 minutes at room temperature. 1,2-dichloroethane solution (2 mL) of methyl (Z)-2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-isobutylami de-2-hexenoate (158 mg, 0.39 mmol) was added dropwise thereto at room temperature and refluxed under heating for 3 hours. The reaction mixture was added an aqueous solution of ammonium chloride and chloroform, and filtered through a pad of celite. The organic layer in the filtrate was separated and the aqueous layer was extracted with chloroform. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residues were subjected to silica gel column chromatography (Flash12M manufactured by Biotage) (chloroform/methanol = 40 : 1) to give 2-{5-{[1-(5-ethoxypyrimidin-2-yl)-2-isopropyl-6-oxo-4-propy 1-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}benzonitril e (111 mg, 58%) as yellow oil. 1H-NMR(CDCl3, 400 MHz)delta: 0.97(3H, t, J = 7.4 Hz), 1.17(6H, d, J = 6.6 Hz), 1.49(3H, t, J=6.9Hz), 1.66-1.77(2H, m), 2.19-2.32(1H, m), 2.60-2.70(2H, m), 3.93(2H, s), 4.10(2H, q, J = 7.1 Hz), 7.45(1H, td, J = 7.7, 1.1 Hz), 7.60 – 7.67(2H, m), 7.73 – 7.80(3H, m), 8.49 (2H, s), 8.67(1H, d, J = 1.3 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39268-74-1, its application will become more common.

Reference:
Patent; Kowa Company Ltd.; MIURA, Toru; SATO, Seiichi; YAMADA, Hajime; TAGASHIRA, Junya; WATANABE, Toshiaki; SEKIMOTO, Ryohei; ISHIDA, Rie; AOKI, Hitomi; OHGIYA, Tadaaki; EP2687523; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 335654-06-3 ,Some common heterocyclic compound, 335654-06-3, molecular formula is C6H4ClN3, 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.

N-Bromosuccinimide (11374.5 g, 64.04 mol, 2.0 eq.) Was added portionwise to a solution of compound III (4907.0 g, 31.91 mol, 1.0 eq.) In acetonitrile Completed, at room temperature (25 ) for 17 hours, monitoring the reaction was complete.The reaction solution was slowly added to 100L of ice water, precipitated a large amount of solid, suction filtration, the filter cake washed with water (50L × 3), dried to obtain 7117.2g white white solid.Yield: 95.82%.1H-NMR (400 MHz, DMSO-d6) delta (ppm) 12.78 (brs, 1H); 8.85 (s, 1H); 7.89 (s, 1H)

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. 335654-06-3, 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Furunkaide Bio-pharmaceutical Co., Ltd.; Rong Liang; Li Jin; Li Hui; Jie Yuanping; Wu Xihan; Yang Minmin; (12 pag.)CN105949196; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia