Day: August 4, 2021

Application of 1193-21-1, Adding some certain compound to certain chemical reactions, such as: 1193-21-1, name is 4,6-Dichloropyrimidine,molecular formula is C4H2Cl2N2, 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 1193-21-1.

Synthesis of 4-Chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine A mixture under N2 of 4,6-dichloropyrimidine (447 mg, 3.00 mmol, 1.00 eq.), 4-(trifluoromethyl)phenylboronic acid (188 mg, 0.99 mmol, 0.33 eq.), Na2CO3 (1.59 g, 15.00mmol, 5.00 eq.) and tetrakis(triphenylphosphine)palladium (0) (173 mg, 0.15 mmol, 0.05eq.) in acetonitrile (5 mL) was stirred at 80 C for 24 hours and further at 100 C for 18hours. The reaction mixture was allowed to cool down to r.t. and concentrated in vacuo.The residue was partitioned between DCM and sat. aq. NaHCO3 soln. The layers were separated. The aq. phase was extracted with DCM. The comb. org. phases were washed with sat. aq. NaCI soln., dried over MgSO4, and concentrated in vacuo. The residue was purified by prep. HPLC (column: Waters X-Bridge, 18×50 mm, 10 tm, UV/MS, basicconditions) and concentrated in vacuo to afford the title compound as a white solid. LC-MS 4: tR = 0.94 mm; [M+H] = 259.3

According to the analysis of related databases, 1193-21-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CIANA, Claire-Lise; KIMMERLIN, Thierry; SIEGRIST, Romain; WO2015/28989; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1193-24-4 , The common heterocyclic compound, 1193-24-4, name is 4,6-Dihydroxypyrimidine, molecular formula is C4H4N2O2, 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.

4,6-Dichloropyrimidine-5-carbaldehyde (9).; In a 5 L 4-neck flask equipped with mechanical stirrer, addition funnel, condenser, thermocouple, and a N2 sweep into an aqueous NaOH scrubbing solution, phosphorous oxychloride (1 L, 10.572 mol, 4.82 equiv) was cooled in an ice/salt bath. N,N-Dimethylformamide (DMF, 320 mL, 4.138 mol, 1.85 equiv) was added dropwise at 0+/-2 C. After addition of 100 mL of DMF (0.5 hr) crystallization occurred and the reaction temperature was increased from 0 to 10 C. Addition was stopped and the mixture was allowed to recool to 2 C. The remaining DMF was added over 2.5 hr at <8 C. The suspension became very thick making stirring difficult. When addition of DMF was complete, the mixture was stirred 0.5 hr at 3-5 C. 4,6-dihydroxypyrimidine (8, 250 g, 2.232 mol) was added portion wise as a solid. After about one third of 4,6-dihydroxypyrimidine was added the reaction mixture became more mobile and a slow exothermic phenomena occurred with the reaction temperature increasing to 12 C. over 0.5 hr. The remaining 4,6-dihydroxypyrimidine was added portion wise over 0.25 hr with the reaction temperature increasing from 12 to 27 C. The reaction temperature was maintained at 25-27 C. with intermittent cooling during which time the yellow suspension became thinner, then thicker once again. After the exothermic phenomenon subsided in about 1 hr, the reaction mixture was heated slowly. At about 55 C. the reaction mixture became extremely thick and the second mild exothermic phenomenon was occurred. The heating mantle was removed while the reaction temperature continued to increase to about 63 C. and remained at this temperature for several minutes before dropping. Heating of the mixture was resumed until gentle reflux (about 100 C.) was attained. At about 95 C. a steady, fairly rapid evolution of HCl began and the reaction mixture gradually thinned and darkened. After about 0.5 hr a clear, brown solution developed with the reflux temperature slowly increasing to 115 C. over 1.25 hr. After a total of 2.5 hr at reflux, the reaction mixture was cooled to room temperature and stirred overnight. Excess POCl3 (as much as possible) was removed under reduced pressure (bath temperature 45-50 C.). The thick residual brown oil was poured very slowly into cold H2O (5 L) in a 20 L separation funnel, adding ice as needed to maintain the aqueous mixture near room temperature. The aqueous mixture was extracted with EtOAc (2×3 L, 1×2 L). The combined EtOAc extracts were washed with H2O (2×2.5 L), saturated NaHCO3 aqueous solution (1 L), brine (1 L), dried over Na2SO4, filtered, and concentrated under reduced pressure (bath temperature at 35 C.) to afford the crude 4,6-dichloropyrimidine-5-carbaldehyde (9, 270 g, 395 g theoretical, 68.4%) as yellow-orange solid. A 20 g portion of this crude material was purified by Kugelrohr distillation (oven temperature at 90-100 C., 225 mTorr) to give 15.3 g of pure 4,6-dichloropyrimidine-5-carbaldehyde (9) as a white solid that turned yellow on standing at room temperature. (On standing crude 9 undergoes slow hydrolysis with formation of HCl. Prior to use in the next step crude 9 was dissolved in a mixture of EtOAc and toluene and filtered to remove insoluble material. The filtrate washed with H2O, saturated NaHCO3 solution, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure and the resulting yellow solid used the following day.) For 9: 1H NMR (CDCl3, 300 MHz) delta ppm 10.46 (s, 1H), 8.89 (s,1H). The synthetic route of 1193-24-4 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Zhou, Jiacheng; Liu, Pingli; Lin, Qiyan; Metcalf, Brian W.; Meloni, David; Pan, Yongchun; Xia, Michael; Li, Mei; Yue, Tai-Yuen; Rodgers, James D.; Wang, Haisheng; US2010/190981; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6328-58-1, 6-Methyl-2-(methylthio)-1H-pyrimidin-4-one, 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, 6328-58-1, blongs to pyrimidines compound. Recommanded Product: 6-Methyl-2-(methylthio)-1H-pyrimidin-4-one

A mixture of 0.01 mol of 6-methyl-2-(methylsulfanyl)-pyrimidin-4(3H)-one and 0.02 mol of pyrrolidine in 20 mL of butan-1-ol was heated for 15 h at 130140C. The solvent was distilled off, the residue was treated with diethyl ether, and the precipitate was ltered off and dried. Yield 72%, mp 240242C. IR spectrum: nu 1646 cm -1 (C=O). 1 H NMR spectrum, delta, ppm: 1.921.99 m (4H, CH 2 CH 2 ), 2.04 s (3H, CH 3 ), 3.433.51 m (4H, CH 2 NCH 2 ), 5.32 s (1H, 5-H), 10.84 br.s (1H, OH). 13 C NMR spectrum, delta C , ppm: 23.7, 24.7, 46.1, 98.8, 152.2, 163.7, 165.1. Found, %: C 60.21; H 7.26; N 23.20. C 9 H 13 N 3 O. Calculated, %: C 60.32; H 7.31; N 23.45.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6328-58-1, its application will become more common.

Reference:
Article; Pivazyan; Ghazaryan; Azaryan, Zh. A.; Yengoyan; Russian Journal of General Chemistry; vol. 89; 10; (2019); p. 2010 – 2017; Zh. Obshch. Khim.; vol. 89; 10; (2019); p. 1511 – 1519,9;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1780-26-3, Adding some certain compound to certain chemical reactions, such as: 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine,molecular formula is C5H4Cl2N2, 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 1780-26-3.

Example 145 Synthesis of 2-(4-{6-[7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-2-methyl-pyrimidin-4-yl}-piperazin-1-yl)-ethanol To synthesize the title compound (CLXIX), two intermediate compounds 62 (2-[4-(6-chloro-2-methyl-pyrimidin-4-yl)-piperazin-1-yl]-ethanol) and 63 (7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine) shown below were used. To synthesize compound 62, to a solution of 4,6-dichloro-2-methyl-pyrimidine (5.0 g, 31 mmol) and 2-piperazin-1-yl-ethanol (2.7 g, 21 mmol) in dioxane (25 mL) was added DIPEA (3.0 mL, 17 mmol). The mixture was heated at reflux for 16 h. The mixture was allowed to cool to room temperature and poured into water. The reaulting aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (5-10% MeOH/DCM) to afford compound 62 as a brown liquid (2.1 g, 39%). MS (ESI+): m/z 257.

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. 1780-26-3, 2-Methyl-4,6-dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TargeGen, Inc.; US2005/245524; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 56-06-4 ,Some common heterocyclic compound, 56-06-4, molecular formula is C4H6N4O, 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.

Synthesis of Compound (37)Intermediate AA (0.5g, 3.96 mmol) was added to a solution of NaOAc (0.647g, 4.76 mmol, 1.2 eq.) in H20 (15 mL). The reaction was heated to 60 C for ~15 minutes, and a solution of 50% aqueous ClCH2CHO (0.5 mL) was then added. The reaction stirred for 2 hours at 60 C. The reaction mixture was filtered to remove undissolved material, and the filtrate stored at 0 C overnight. The resulting precipitated solid was collected by filtration, washed with cold H20, and dried to obtain Compound (37) (120mg, 20%) as a pink solid. Rf = 0.7 (30%MeOH/CHCl3/0.2 mL of aqueous NH3). 1H-NMR (400MHz, DMSO-_¾ delta 10.95 (br. s, exchanged with D20, 1H), 10.20 (s, exchanged with D20, 1H), 6.60 (dd, J = 3.2, 2.0Hz, 1H), 6.18 (dd, J = 3.2, 2.0Hz, 1H), 6.03 (br. s, exchanged with D20, 2H). Mass (m/z): 150.8 (M++l). LCMS: (Column: Zodiacsil 120-5-C-18-Aq (4.6 * 50 mm), Mobile phase: A: 0.01M HCOONH4 (Aq); B: MeOH, T/%B: 0/5, 10/90, 10.1/5, Flow: 1.0 mL/min, Diluent: MeOH), Rt=2.599 min, 99.16 (214 nm), 99.10 (254 nm).

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. 56-06-4, 2,6-Diaminopyrimidin-4(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian; WO2011/35009; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 3680-69-1

38.4 g (250.4 mmol, 1.0 eq.) with stirring in an ice bath. 4-chloro-7H-pyrrole [2,3-d]pyrimidine is dissolved in 200 mL of dry DMF solution.13 g (305 mmol, 1.2 eq) of 57% NaH was added. The reaction was stirred at room temperature for 1 hour, then 50.9 g of SEMCl (305 mmol, 1.2 eq.).After the addition, the reaction was stirred in an ice bath for 1 hour. quenched with water, extracted with ethyl acetate. the title compound (71 g, yield = 100%) was obtained.

With the rapid development of chemical substances, we look forward to future research findings about 3680-69-1.

Reference:
Patent; Beijing Puqi Pharmaceutical Technology Co., Ltd.; Zhu Li; Hu Wei; Wang Jin; (32 pag.)CN109867675; (2019); A;,
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.36315-01-2, name is 2-Amino-4,6-dimethoxypyrimidine, molecular formula is C6H9N3O2, molecular weight is 155.16, as common compound, the synthetic route is as follows.Computed Properties of C6H9N3O2

To 50 ml pear-shaped flask add 155 mg (1 mmol) of 2 – amino – 4, 6 – dimethoxy pyrimidine solid and 8 ml of dried DMF, stirring to dissolve adding 2 g water-free K2CO3, Stirring under the room temperature condition 0.5 h, then to slow added in the reaction system of 270 mg (1 mmol) of 5 – bromo valeric acid O-methyl ester, stir at room temperature overnight TLC monitoring to the reaction is complete. After the reaction is finished adding 40 ml of water, then 2 × 50 ml ethyl acetate, the combined organic phase sequentially for 2 × 50 ml of 1 N HCl solution, 2 × 50 ml of saturated sodium chloride solution. The organic phase after drying over anhydrous sodium sulfate the solvent is removed by reduced pressure distillation after purification on silica gel, ethyl acetate/petroleum ether (v/v, 4/1) elution, to obtain light yellow oily liquid, yield 72%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36315-01-2, 2-Amino-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Northwest A&F University; Ji Zhiqin; Wei Shaopeng; (12 pag.)CN107857735; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 916420-27-4, name is tert-Butyl 2,4-dichloro-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. name: tert-Butyl 2,4-dichloro-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

Step 1- tert-butyl 2-chloro-4-(pyridin-4-yl)-5,6-dihydropyrido[3,4-d]pyrimidine- 7(8H)-carboxylate (ij): 4-(Tributylstannyl)pyridine (247 mg, 0.671 mmol), t-butyl 2,4- dichloro-5,6-dihydropyrido-[3,4-d]pyrimidine-7(8H)-carboxylate (bx) (200 mg, 0.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (76 mg, 0.066 mmol) were dissolved in 1,4- Dioxane (7 mL). The reaction was micro waved at 1300C for 20 minutes The reaction mixture was concentrated on silica gel and purified by flash chromatography (100% Hex to 80% EtOAc/Hex) to give compound ij as a white solid: LC/MS: m/z = + 347.8 (M +H)+.

With the rapid development of chemical substances, we look forward to future research findings about 916420-27-4.

Reference:
Patent; GENENTECH, INC.; BERGERON, Philippe; COHEN, Frederick; ESTRADA, Anthony; KOEHLER, Michael, F. T.; LAU, Kevin, Hon Luen; LY, Cuong; LYSSIKATOS, Joseph, P.; ORTWINE, Daniel, Fred; PEI, Zhonghua; ZHAO, Xianrui; WO2010/14939; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 171887-03-9, 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 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 82 25 (20 g, 53 mmol) in 85 n-BuOH (300 mL) was added 86 DIPEA (28 mL) and 90 2-amino-4,6-dichloro-5-formamidopyrimidine (13.2 g, 64 mmol). Resulting mixture was heated in a sealed vessel at 160 C. for 24 h. Volatiles were evaporated, column chromatography (70 AcOEt in 29 toluene 20-100%) afforded title compound (21 g, 75%) as a light yellow solid: 1H NMR (401 MHz, DMSO-d6) delta 8.25 (s, 1H), 6.81 (s, 2H), 4.87 (t, J=5.3 Hz, 1H), 4.74 (q, J=9.5 Hz, 1H), 4.49 (dd, J=9.6, 4.2 Hz, 1H), 4.01 (d, J=4.1 Hz, 1H), 3.57 (ddd, J=11.0, 8.0, 5.2 Hz, 1H), 3.49 (dt, J=11.0, 5.6 Hz, 1H), 2.27 (dt, J=13.4, 9.7 Hz, 1H), 2.11-2.01 (m, 1H), 1.76 (ddd, J=14.0, 9.5, 5.2 Hz, 1H), 0.91 (s, 9H), 0.65 (s, 9H), 0.11 (s, 3H), 0.08 (s, 3H), -0.16 (s, 3H), -0.51 (s, 3H); 13C NMR (101 MHz, DMSO-d6) delta 159.56, 154.42, 149.50, 142.87, 124.09, 75.99, 74.55, 63.22, 58.88, 46.12, 27.71, 26.05, 25.66, 18.01, 17.61, -4.31, -4.42, -5.54; ESI MS m/z (%): 528.3 (100) [M+H], 550.2 (49) [M+Na]; HRMS ESI (C23H43O3N5ClSi2) calculated: 528.25875; found: 528.25868.

According to the analysis of related databases, 171887-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY ASCR,V.V.I.; Birkus, Gabriel; Pav, Ondrej; Jandusik, Tomas; Rosenberg, Ivan; Nencka, Radim; US2019/185510; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2435-50-9, 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. 2435-50-9, name is Pyrimidine-4-carbaldehyde, molecular formula is C5H4N2O, 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: SI, Figure 4. General procedure of the reductive amination reactions: synthesis of AA9-AA24 compounds (Tables 1 and 2). The ethyl 3-amino-4-(cyclohexylamino)benzoate (AA1) and derivatives (1 equiv.)and benzaldehyde (1 equiv) were heated in DCE for 1h at 80 oC in the presence of molecular sieves (4 A), then the mixture was cooled down to room temperature before addition of the NaBH(OAc)3 (1.6 equiv.) in small portions over 3h. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 17h. The reaction mixture was quenched with aqueous saturated NaHCO3, and the product was extracted with EtOAc. The EtOAc extract was dried (MgSO4), and the solvent was evaporated. The residue was purified by flash-column chromatography on silica gel, using a mixture of solvent of DCM: MeOH (50:1), to provide the desired AA9-AA24 compounds (Tables 1-2).

According to the analysis of related databases, 2435-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iniguez, Eva A.; Perez, Andrea; Maldonado, Rosa A.; Skouta, Rachid; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5315 – 5320;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia