Category: pyrimidines

Reference of 22536-65-8, 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. 22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, 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.

General procedure: To a solution of 1.0 eq. of VII and 1.20 eq. of a 2-halopyrimidine in H20 and dioxane was added 2.0 eq. of potassium fluoride. The mixture was subjected to microwave irradiation maintaining a reaction temperature of 120 C for 1 h. The solvent was removed in vacuo, andthe residue was purified by chromatography.

According to the analysis of related databases, 22536-65-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); 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.26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine, molecular formula is C10H6Cl2N2, molecular weight is 225.074, as common compound, the synthetic route is as follows.category: pyrimidines

To a 250 mL flask was added a mixture of 5.0 g (22.22 mmol) of Intermediate L-3, 22.09 g (51.1 mmol) of L-6, 7.68 g (55.54 mmol) of potassium carbonate, 1.28 g of Tetrakis (triphenylphosphine) palladium (1.11 mmol) were dissolved in 100 mL of tetrahydrofuran and 30 mL of water, and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resultant mixture was added to 500 mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel / celite, and then an organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain Compound A-55 (12.68 g, 75% yield). The result of elemental analysis of the resulting Compound A-55 is as follows.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Samsung SDI Co., Ltd.; Lee, Sung Jae; Kim, Byoung Gu; Kim, Young Kwan; Min, Soo Hyoun; Saw, Ju Hee; Yun, Uhn Son; (42 pag.)KR2016/19747; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 874-14-6, 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. 874-14-6, name is 1,3-Dimethyluracil, molecular formula is C6H8N2O2, 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.

0.14 g (1.0 mmol) of 1,3-dimethyluracil was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.2 ml of a 30percent hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 mol/l aqueous solution of ferric sulfate. The mixture was stirred at 40 to 50¡ãC for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 1,3-dimethyl-5-trifluoromethyluracil (19F-NMR yield: 78percent) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 1,3-Dimethyl-5-trifluoromethyluracil was obtained as a white solid (0.12 g, yield: 44percent) by preparative thin-layer chromatography. 1H-NMR (deuterated acetone): delta3.25(s, 3H), 3.51(s, 3H), 8.23(q, JHF=1.05Hz, 1H). 13C-NMR (deuterated acetone): delta27.8, 37.6, 102.9(q, JCF=32.3Hz), 123. 8 (q, JCF=268.4Hz), 146.4 (q, JCF=5. 91Hz), 151.9, 159.5. 19F-NMR (deuterated acetone): delta-60.6. MS (m/z): 208[M]+.

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 874-14-6, 1,3-Dimethyluracil.

Reference:
Patent; Tosoh Corporation; Tosoh F- Tech Inc.; SAGAMI CHEMICAL RESEARCH CENTER; EP1947092; (2008); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 444731-75-3, 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. 444731-75-3, name is N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine. A new synthetic method of this compound is introduced below.

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, 1 .Oequiv) at room temperature. The reaction mixture was heated at reflux for 3 h, then 4 M HCI in 1 ,4-dioxane (18 muL, 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 CH3CINI and dried in the air to yield 1.3 g (73%) of 5-({4- [(2,3-dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl}amino)-2-methyl benzenesulfonamide monohydrochloride as an off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,444731-75-3, N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-amine, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/20564; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 933702-55-7 ,Some common heterocyclic compound, 933702-55-7, molecular formula is C5H3ClN2O, 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 2-chloropyrimidine5-carhaldehyde (0.5 g, 3.5 mmol) in chloroform (10 mL), add diethyiaminosuifur trioxide (567 mg, 3,5 mmoi), then reflux for 1 hour. Cool the mixture to ambient temperature and quench with 1-120. Separate the layers, wash the organic fraction with 1-120 (2x), dry over Mg504, filter, collect the filtrate, and concentrate the filtrate under reduced pressure to provide the title product (327 mg, 51%),

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. 933702-55-7, 2-Chloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; ESCRIBANO, Ana Maria; GONZALEZ, Maria Rosario; LAFUENTE BLANCO, Celia; MARTIN-ORTEGA FINGER, Maria Dolores; WILEY, Michael R.; (82 pag.)WO2016/187384; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10325-70-9, 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.10325-70-9, name is 5-Acetylpyrimidine, molecular formula is C6H6N2O, molecular weight is 122.1246, as common compound, the synthetic route is as follows.

Preparation 84 (R)-N-((5)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane- 2-sulfinamide To a solution of l-(pyrimidin-5-yl)ethanone (2.072 g, 16.97 mmol) in DMF (40 mL) was added 60 % wt aH (0.747 g, 18.66 mmol) at 0 C under nitrogen. The mixture was stirred at 0 C for 30 min. A solution of (R,¡ê)-N-(l-(2,4-difluorophenyl)ethylidene)-2- methylpropane-2-sulfinamide from preparation 73 (2.2 g, 8.48 mmol) in DMF (4 mL) was slowly added at -10 C under nitrogen. The mixture was stirred from -10 C to -5 C over 1.5 h. The reaction was quenched with water, and extracted with 2×250 mL of ethyl acetate. The combined organic layers were removed, dried over sodium sulfate, and concentrated. The residue was purified via silica gel chromatography (gradient elution using ethyl acetate to 10% methanol in ethyl acetate) to give (R)-N-((5)-2-(2,4- difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane-2-sulfinamide (1.5 g, 3.93 mmol, 46.4 % yield). MS (M+H)+ = 382.05. 1H NMR (500MHz, CHLOROFORM-d) delta 9.37 (s, 1H), 9.18 (s, 2H), 7.61 (td, J=9.3, 6.5 Hz, 1H), 6.97 – 6.89 (m, 1H), 6.74 (ddd, J=12.9, 8.4, 2.6 Hz, 1H), 5.32 (s, 1H), 4.21 (dd, J=18.6, 1.4 Hz, 1H), 3.91 (dd, J=18.6, 2.9 Hz, 1H), 1.86 (s, 3H), 1.34 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 10325-70-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WU, Yong-Jin; GUERNON, Jason M.; WO2014/98831; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 6622-92-0, Adding some certain compound to certain chemical reactions, such as: 6622-92-0, name is 2,6-Dimethylpyrimidin-4-ol,molecular formula is C6H8N2O, 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 6622-92-0.

b) In analogy to example 12b), from 2,4-dimethyl-6-hydroxypyrimidine (1.5 g, 12 mmol) and piperonal (1.8 g, 12 mmol) in acetic anhydride there was obtained (E)-2-(2-benzo[1,3]dioxol-5-yl-vinyl)-6-methyl-pyrimidin-4-ol (0.76 g, 24.5%) as a yellow solid. EI mass spectrum, m/e: 256 (M calculated for C14H14N2O3: 256).

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; Breu, Volker; Dautzenberg, Frank; Mattei, Patrizio; Neidhart, Werner; Pflieger, Philippe; US2002/86858; (2002); 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. 1005-37-4, name is 6-Chloro-N4-methylpyrimidine-2,4-diamine, molecular formula is C5H7ClN4, 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. name: 6-Chloro-N4-methylpyrimidine-2,4-diamine

Example 3296-[4-(Aminomethyl)phenyl]-4-N-methylpyrimidine-2,4-diamine.Tetrakis(triphenylphosphine)palladium (0) (5 mol%) was added to a stirredmixture of 6-chloro-4-N-methylpyrimidine-2,4-diamine (1.00 mmol), [4-(aminomethyl)phenyl]boronic acid (1.3 eq.), sodium carbonate (4.2 eq.), dioxane(4 ml) and water (1 ml) in a tube. The tube was sealed and the reaction washeated at 90C overnight. The solvent were removed in vacuum and to theremaining solid was added ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate. The crude material was then purified by flash chromatography (0-*15 % MeOH/DCM) to give the title compound. LCMS [M+H] 230; 1H NMR (400 MHz, DMSO-d6) OH ppm 7.86 (2 H, d, J=7.58Hz), 7.38 (2 H, d, J=8.59 Hz), 6.19 (1 H, 5), 5.96 (2 H, 5), 3.76 (2 H, 5), 2.79 (3 H, d, J=4.80 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 1005-37-4.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; HELLEDAY, Thomas; KOOLMEISTER, Tobias; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; WO2014/84778; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5750-76-5 , The common heterocyclic compound, 5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

(2-aminophenyl)dimethyl phosphorus oxide (8.76 g, 51.81 mmol), 2,4,5-trichloropyrimidine (14.92 g, 81.35 mmol), anhydrouspotassium carbonate (22.49 g, 162.29 mmol) and N,N-dimethylformamide (50 mL) were added in a 100 mLsingle-necked flask, and the mixture was heated to 60C and reacted for 5 hours. After the reaction was completed, thereaction solution was cooled down to room temperature, added with water (30mL) and extracted with dichloromethane(100 mL 3 3), washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered by suction, andevaporated under reduced pressure to remove the solvent. The resulting crude product was subjected to silica gelcolumn chromatography (mobile phase, dichloromethane : methanol = 40 : 1) to give (2-((2,5-dichloropyrimidin-4-yl)amino)phenyl)dimethyl phosphorus oxide (11.3 g, 69.0% yield).1H-NMR (300 MHz, CDCl3) : delta = 11.55 (s, 2H), 8.67 (dd, J = 4.4, 8.5 Hz, 1H), 8.22 (s, 1H), 7.59 (dd, J = 7.7, 8.1 Hz,1H), 1.86 (s, 3H), 1.82 (s, 3H). 13C-NMR (75 MHz, CDCl3) : delta = 156.85, 155.10, 133.05, 133.03, 129.77, 129.63, 123.56,123.40, 122.18, 122.09, 19.28, 18.33.HRMS (ESI, [M+H]+) m/z: 316.0175.

The synthetic route of 5750-76-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; ZHANG, Yinsheng; LIU, Baomin; YANG, Beibei; (35 pag.)EP3381925; (2018); 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.7504-94-1, name is 2-Hydrazinylpyrimidine, molecular formula is C4H6N4, molecular weight is 110.1172, as common compound, the synthetic route is as follows.HPLC of Formula: C4H6N4

After adding 40 mg of 2-dimethylaminoethanol, 120 mg of triphenylphosphine and 0.200 ml of DEAD (2.2 M, toluene solution) to a 1 ml THF solution containing 100 mg of {2-(3-hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (4c)) at 0 C., the mixture was stirred at room temperature for 16 hours and 30 minutes. The reaction mixture was concentrated, and the residue was crudely purified by silica gel column chromatography (ethyl acetate-heptane) to give 55 mg of a crude product. To a 1 ml DMF solution containing 55 mg of the obtained crude product there were added 12 mg of 2-hydrazinopyrimidine and 0.015 ml of triethylamine, and the mixture was stirred at 85 C. for 11 hours and 30 minutes under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 0.8 ml of methanol, 0.8 ml of THF and 0.1 ml of acetic acid. Next, 100 mg of sodium cyanotrihydroborate was added to the solution and the mixture was stirred at room temperature for 3 hours and 30 minutes. The reaction mixture was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product. To a solution of the obtained crude product in 2.4 ml of a methanol:water:acetic acid=1:1:1 mixed solvent there was added 100 mg of iron powder, and the mixture was stirred at 65 C. for 18 hours and 30 minutes under a nitrogen atmosphere. After filtering the reaction mixture, it was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product. The obtained crude product was optically resolved using a SUMICHIRAL OA-2500 column, and the first eluting enantiomer (4.35 mg) of the title compound was obtained as a light yellow solid. 1H-NMR (CD3OD) delta 1.92 (s, 6H) 2.49 (s, 6H) 2.96 (dd, J=5.2, 5.6 Hz, 2H) 3.76 (s, 3H) 4.14 (dd, J=5.2, 5.6 Hz, 2H) 5.58 (s, 1H) 6.47 (t, J=2.0 Hz, 1H) 6.77 (t, J=2.0 Hz, 2H) 6.85 (d, J=8.8 Hz, 2H) 7.30 (t, J=4.8 Hz, 1H) 7.60 (d, J=8.8 Hz, 2H) 8.77 (d, J=4.8 Hz, 2H) HPLC retention time: 11 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7504-94-1, 2-Hydrazinylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2008/15199; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia