Month: March 2022

Electric Literature of 87253-62-1, Adding some certain compound to certain chemical reactions, such as: 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid,molecular formula is C8H8N4O2, 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 87253-62-1.

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

According to the analysis of related databases, 87253-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3974-16-1 , The common heterocyclic compound, 3974-16-1, name is 4,6-Dichloro-5-phenylpyrimidine, molecular formula is C10H6Cl2N2, 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.

C. Preparation of 4-chloro-6-(4-chlorophenyl)-5-phenylpyrimidine To a mixture of 4,6-dichloro-5-phenylpyrimidine (675 mg, 3.0 mmol), 4-chlorophenylboronic acid (704 mg, 4.5 mmol) and tetrakis(triphenylphosphine)palladium (173 mg, 0.15 mmol) in toluene (10 mL) at room temperature under argon was added aqueous Na2CO3 solution (2 M, 3 mL, 6 mmol). The resulting reaction mixture was stirred at 100 C. under argon for 5 h, after which time analysis by HPLC/MS indicated that the the reaction was complete. After cooling the reaction mixture to room temperature, water (15 mL) was added. The resulting mixture was extracted with EtOAc (2*25 mL). The combined organic layers were washed with saturated aqueous NaCl, then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluted with ethyl acetate-hexanes to obtain 571 mg of the title compound as a white solid. HPLC/MS: retention time=3.85 min, [M+H]30 =301.

The synthetic route of 3974-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wu, Gang; Mikkilineni, Amarendra B.; Sher, Philip M.; Murugesan, Natesan; Gu, Zhengxiang; US2006/287341; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 84341-13-9, 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. 84341-13-9, name is 8-Chloropyrido[3,4-d]pyrimidin-4-ol, molecular formula is C7H4ClN3O, 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 stirred suspension of 8-chloropyrido[3,4-d]pyrimidin-4(3H)-one (3) (110 g, 0.61 mol) in DMF (1.6 L) was added tert-butyl piperazine-1-carboxylate (135 g, 0.73 mol) and BOP (402 g, 0.91 mol), followed by DBU (184 g, 1.2 mol). The resulting solution was stirred at 25 C. for 6 hours. The crude reaction mixture was monitored by LCMS and showed most of the starting material was consumed. The mixture was diluted with ice water (7 L), and extracted with EtOAc (4*1.5 L). The combined organic layers were washed with water (3*3 L), brine (2 L), dried over Na2SO4, and concentrated which gave the crude product. The crude product was purified by silica gel chromatography and eluted with 5% methanol/DCM and gave tert-butyl 4-(8-chloropyrido[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylate (4) as a light yellow solid (101 g, 47% yield). 1H NMR (400 MHz, CDCl3) delta 8.89 (s, 1H), 8.34 (d, J=5.7 Hz, 1H), 7.58 (d, J=5.7 Hz, 1H), 4.13-3.79 (m, 4H), 3.66 (dd, J=6.2, 4.1 Hz, 4H), 1.50 (s, 9H). LCMS (ESI) m/z 350, 352 (M+H).

According to the analysis of related databases, 84341-13-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; PLANKEN, Simon; CHENG, Hengmiao; COLLINS, Michael Raymond; SPANGLER, Jillian Elyse; BROOUN, Alexei; MADERNA, Andreas; PALMER, Cynthia; LINTON, Maria Angelica; NAGATA, Asako; CHEN, Ping; US2019/233440; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 114040-06-1, Adding some certain compound to certain chemical reactions, such as: 114040-06-1, name is 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine,molecular formula is C6H2BrCl2N3, 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 114040-06-1.

To a solution of 3-bromo-5,7-dichloropyrazolo [1,5-a] pyrimidine (0.14 g, 0.53 MMOL) in ethanol (20 cm3) was added 4-AMINO-N, N- dimethbenzenesulphonamide (0.107 g, 0.53 mmol). The reaction was heated at reflux for 16 h. The reaction was concentrated in vacuo and the residue triturated with hot ETHANOL (2 X 10 CM3) to yield the product as a white solid (0. 10 G, 43%). 8H (400 MHz; D4-CDC13) 8.10 (1H, s), 7.89 (2H, d, J 6.7), 7.66 (2H, d, J6. 7), 6.51 (1 H, s), 2.74 (6H, s). M/Z430, 432 and 434 each (M+H, 75 %, 100% and 25%), retention time 2. 58 min (Method A).

According to the analysis of related databases, 114040-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERNALIS (CAMBRIDGE) LIMITED; WO2004/87707; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1007-11-0 , The common heterocyclic compound, 1007-11-0, name is 6-Chloro-N4,N4-dimethylpyrimidine-2,4-diamine, molecular formula is C6H9ClN4, 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 mixture of theta-chloro-LambdaLambdaLambda^-dimethyl^^-pyrimidinediamine (500 mg, 2.90 mmol), 2- acetyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,2-dihydroindazolo[4,3- 6c][1 ,5]benzoxazepine (1.47 g, 3.77 mmol), tricyclohexylphosphine (20 mg, 0.07 mmol), and K2CO3 (1.22 g, 8.7 mmol) in 1 ,4-dioxane (4 ml.) and water (6 ml.) was added Pd2(dba)3 (26 mg, 0.03 mmol) under nitrogen, and the reaction mixture was heated for 40 minutes at 140 0C in a microwave reactor. The mixture was cooled to room temperature and filtered, and the resulting solid was washed with EtOAc and purified by reverse phase HPLC (gradient: 20% CH3CN/H2O to 95% CH3CN/H2O w/0.04% NH4OH) to afford the title compound (96 mg, 9%) as a pale yellow solid. LC-MS (ES) m/z = 360 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 3.1 1 (s, 6H), 6.12 (s, 2H), 6.55 (s, 1 H), 6.89 – 6.92 (m, 1 H), 7.06 – 7.10 (m, 1 H), 7.30 – 7.33 (m, 2H), 7.48 (s, 1 H), 7.87 (s, 1 H), 9.54 (s, 1 H).

The synthetic route of 1007-11-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; BRADY, Gerald, Patrick, Jr.; GALLAGHER, Timothy, Francis; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; WO2010/120854; (2010); 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 1582-25-8, name is 4-Chloro-6-methyl-2-trifluoromethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-Chloro-6-methyl-2-trifluoromethylpyrimidine

Step A: (±)-tert-butyl-2-methyl-3-((6-methyl-2-(trifluoromethyl)pyrimidin-4-yl)amino)piperidine-1-carboxylate. To intermediate B-3 (135 mg, 0.63 mmol) in DMF (1.5 mL) was added Cs2CO3 (308 mg, 0.95 mmol) and 4-chloro-6-methyl-2-(trifluoromethyl)pyrimidine (149 mg, 0.76 mmol). The flask was then heated with an oil bath at 70 C. for 18 h. The reaction was allowed to cool to rt, diluted with H2O and extracted with EtOAc (2×). The combined organics were washed with brine and dried (Na2SO4). Silica gel chromatography ( EtOAc in hexanes) gave the title compound (111 mg, 47%). MS (ESI) mass calcd. for C17H25F3N4O2, 374.2; m/z found 275.2 [M+H-100]+. 1H NMR (CDCl3): 6.24 (s, 1H), 5.44 (s, 1H), 4.48-4.31 (m, 1H), 4.15-3.60 (m, 2H), 2.97-2.78 (m, 1H), 2.42 (s, 3H), 1.85 (s, 2H), 1.74-1.32 (m, 10H), 1.26 (d, J=7.0 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1582-25-8.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Dvorak, Curt A.; Shireman, Brock T.; US2014/275095; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 17180-94-8, 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. 17180-94-8, name is 5-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.

General procedure: To a solution of the nitrile / sulfone (1.2 mmol) in THF (5 ml) at -78 oC (under an N2atmosphere) was added LiHMDS (1.2 mL of 1 M in THF, 1.2 mmol) dropwise and thereaction mixture was stirred at this temperature for 5 minutes. The heterocycle (1 mmol,1 eq.) was added at while the reaction mixture was at -78oC, the cooling bath wasremoved and the reaction mixture was stirred until the reaction was judged complete byLCMS analysis (generally 1 h). Solid KMnO4 (316 mg, 2 mmol, 2 eq.) and acetonitrile(1 ml) were added and the reaction mixture was stirred at room temperature until thereaction was judged complete by LCMS analysis (generally 4-6 h). The reaction mixturewas poured into saturated aqueous NaHCO3 and the layers separated. The aqueous layerwas then extracted with EtOAc (3x). All organics were combined, washed with water,brine, dried (Na2SO4) and evaporated to dryness. Purification by silica gel columnchromatography (12 g Isco silica cartridge) using hexanes and EtOAc gave the desiredproducts.

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 17180-94-8, 5-Chloropyrimidine.

Reference:
Article; Anderson, Corey; Moreno, Jesus; Hadida, Sabine; Synlett; vol. 25; 5; (2014); p. 677 – 680;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 943006-46-0, 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 943006-46-0, name is 4-Amino-6-iodo-2-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Part C: A mixture of 4-amino-6-diodo-2-methylpyrimidine (500 mg, 2.13 mmol) and NaH (60% dispersion in mineral oil, 170 mg, 4.25 mmol) in DMF (15 mL) was stirred at RT for 30 min. A solution of Intl-A (741 mg, 2.13 mol) in DMF (7 mL) was added, and the reaction mixture was stirred at RT for 1 h. The reaction mixture was poured into EtOAc (ca. 100 mL) and water (ca. 25 mL), IM aqueous HCl was added to give pH = 7, and the layers were separated. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography, elution with 40-75% EtOAc in hexanes, to give Int-6 (710 mg, 66%) as an off-white solid. LCMS (m/z): 503 (M+H)+

According to the analysis of related databases, 943006-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ICAGEN, INC.; WO2007/75852; (2007); 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. 14631-08-4, name is 2-Chloropyrimidine-4,5-diamine. A new synthetic method of this compound is introduced below., Safety of 2-Chloropyrimidine-4,5-diamine

Intermediate 82: Mixture /V-(5-amino-2-chloro-4-pyrimidinyl)-2-oxo-3-phenyl-1-oxa-3- azaspiro[4.51decane-8-carboxamide and lambda/-(4-amino-2-chloro-5-pyrimidinyl)-2-oxo-3- phenyl-1-oxa-3-azaspiro[4.51decane-8-carboxamide; (Trans^-oxo-S-phenyl-i-oxa-S-azaspiro^.deltaJdecane-delta-carboxylic acid (Intermediate 10 alternative preparation, 239 mg, 0.286 mmol), 2-chloro-4,5-pyrimidinediamine (commercially available, 41.4 mg, 0.286 mmol) and EDC HCI (88 mg, 0.458 mmol) were dissolved in pyridine (2 ml) and stirred at room temperature overnight. The solvent was removed under vacuum to give a residue which was purified by silica gel chromatography (5g cartridge) eluting in gradient with CyclohexaneEtOAc 9:1 to 1 :1 then DCMMeOH 95:5 to afford the title compound as a pale yellow solid (35 mg, 30%), mixture of regio and stereoisomers with unknown ratio). UPLC-MS: 0.60 min, m/z 402 [M+H]+.

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, 14631-08-4, 2-Chloropyrimidine-4,5-diamine.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 60331-15-9, Adding some certain compound to certain chemical reactions, such as: 60331-15-9, name is 4-Chloro-6-methoxy-2-methyl-5-nitropyrimidine,molecular formula is C6H6ClN3O3, 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 60331-15-9.

EXAMPLE 4 3-(6-Methoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine A solution of 0.204 g (1.0 mmol) of 2-methyl-4-methoxy-5-nitro-6-chloro-pyrimidine [Helv. (1958), 41, 1806], 0.20 g (1.1 mmol) 2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride [J. Heterocycl. Chem. (1971), 8(5), 779-83] and 0.30 g (3.0 mmol) triethylamine in 10.0 ml N,N-dimethylformamide was stirred at room temperature for 60 h. The reaction mixture was then poured into 50 ml of an ice/water mixture and extracted three times with 60 ml of dichloromethane. The combined organic phases were washed twice with 50 ml of water, dried over magnesium sulphate, evaporated under reduced pressure and dried in a high vacuum. The residue obtained was then crystallized from dichloromethane/hexane to yield 0.28 g (0.9 mmol), 90%,3-(6-methoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow solid; m.p. 123-128 C.

According to the analysis of related databases, 60331-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US6218385; (2001); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia