Category: pyrimidines

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

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;,
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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;,
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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;,
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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;,
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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;,
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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 32998-03-1, name is 2,6-Dichloro-N-methylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. name: 2,6-Dichloro-N-methylpyrimidin-4-amine

EXAMPLE 42 N-Methyl-2,6-di-(4′-t-butoxycarbonyl-1′-piperazinyl)-4-pyrimidinamine (V) A mixture of 2,6-dichloro-4-methylaminopyrimidine (III, EXAMPLE 1, 5 g) dissolved in o-xylene (300 ml) is treated with mono-t-BOC-piperazine (IV, 20.92 g) and the reaction mixture is refluxed for 50 hr. The reaction mixture is concentrated under reduced pressure. The resulting residue is partitioned between chloroform and saturated sodium bicarbonate. The organic layer is separated, washed with saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product (24.53 g) is chromatographed on silica gel (590 g). The column is packed and eluted with chloroform/acetone (97/3). An initial fraction of 400 ml is collected followed by 8 ml fractions. Based on their TLC homogeneity, fractions 132-326 are combined and concentrated to give the title compound, NMR (CDCl3, TMS) 4.94, 4.96, 3.75-3.65, 3.55-3.4, 2.85 and 1.48 8; MS (m/z) M+ (found) 477, other ions at m/z 420, 376, 364, 348, 321,265, 221, 178, 164 and 57.

With the rapid development of chemical substances, we look forward to future research findings about 32998-03-1.

Reference:
Patent; The Upjohn Company; US5502187; (1996); A;,
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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. 138538-42-8, name is 6-Methylpyrimidine-4-carboxylic acid. A new synthetic method of this compound is introduced below., Safety of 6-Methylpyrimidine-4-carboxylic acid

Preparative Example 8; Step A; To a 500 ml round bottom flask was added 400 mL H2O and KMnO4 (140 mmoles) and then commercially available 4,6-dimethyl-pyrmidine (35 mmole) and mixture refluxed for 20 hours. The mixture was filtered through celite and then acidified to pH 3. The aqueous was then evaporated under reduced pressure to give a solid. To the solid was then added 300 ml of methanol saturated with dry HCl. The mixture was then refluxed for 15 hours. The volatile components of the reaction mixture was then removed under reduced pressure to give an oil. To the oil was then added 150 ml of methylene chloride and organic washed with saturated NaHCO3. The aqueous was removed and then the organic layer was dried over MgSO4, filtered and then the volatile components removed under reduced pressure to give and oil. The oil was purified by column chromatography (SiO2, 10% either-methylene chloride) to give 6-methyl-pyrimidine-4-carboxylic acid.

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, 138538-42-8, 6-Methylpyrimidine-4-carboxylic acid.

Reference:
Patent; Alantos Pharmaceuticals Holding, Inc.; US2008/21024; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Related Products of 1159981-95-9, 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 1159981-95-9, name is 5-Bromopyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromopyrazolo[1,5-a]pyrimidine (200 mg, 1.00 mmol), Pd(PPh3)4 (117 mg, 0.101 mmol), copper(I) iodide (96 mg, 0.101 mmol), and hexa-n-butylditin (0.51 mL, 1.0 mmol) in toluene (0.5 mL) at 110 C. was added ethyl (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate (0.50 g, 1.0 mmol) in toluene (3 mL) over 30 minutes. Reaction mixture was stirred nine hours at 110 C., cooled to room temperature. Ethyl acetate and lithium chloride were added and stirred over the weekend. Reaction mixture was filtered, concentrated and purified by CombiFlash (ethyl acetate/hexanes) to give desired product. LCMS-ESI+: calc’d for C28H28ClN4O3S: 535.2 (M+H+); Found 535.2 (M+H+).

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 1159981-95-9, 5-Bromopyrazolo[1,5-a]pyrimidine.

Reference:
Patent; Gilead Sciences, Inc.; Cai, Zhenhong R.; Guo, Hongyan; Ji, Mingzhe; Jin, Haolun; Lee, Amy; McFadden, Ryan; Mitchell, Michael L.; Munoz, Manuel; Pyun, Hyung-Jung; Xu, Lianhong; Yang, Hong; (272 pag.)US2018/118734; (2018); A1;,
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Electric Literature of 1122-44-7 , The common heterocyclic compound, 1122-44-7, name is 4-Amino-5-iodopyrimidin-2(1H)-one, molecular formula is C4H4IN3O, 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 stirred solution of 4-amino-5-iodouracil (200 mg, 0.84 mmol) in anhydrous dimethylformamide (15 mL) at room temperature in a nitrogen atmosphere were added tetrakis (triphenyl phosphine)palladium (98 mg, 0.08 mmol), copper(I)iodide (32 mg, 0.17 mmol), diisopropylethylamine (0.28 mL, 1.7 mmol) and 1-phenylacetylene (0.33 mL, 2.53 mmol). The reaction mixture was stirred at room temperature. After 22 h, 10 drops of 5% of the disodium salt of EDTA/H2O were added to the reaction mixture, and the mixture was concentrated in vacuo. The residue obtained was purified on silica gel column using MeOH/CHCl3 (4:96, v/v) as an eluent to give 7. This was obtained as a solid in 67% yield; mp > 250 C; 1H NMR (DMSO-d6): delta 6.93 (s, 1H, NH2), 7.40 (m, 3H, C6H5), 7.60 (m, 2H, C6H5), 7.66 (s, 1H, NH2), 7.83 (s, 1H, H-6), 11.01 (br s, 1H, NH); 13C NMR (DMSO-d6): delta: 56.48 (C-beta), 82.30 (C-alpha), 94.18 (C-5), 128.75, 128.90, 131.61 (C-phenyl), 147.30 (C-6), 155.52 (C-2), 165.30 (C-4). FTIR (KBr) cm-1: 3461 (Ar C-H), 3399 (NH), 3139 (NH2), 2219 (C?C), 1890, 1657 (C=O), 1457, 1230, 1027, 911, 749, 687, 559 cm-1. Anal. C12H9N3O (M.W. 211.12). Calcd C 68.24, H 4.29, N 19.8. Found C 68.64, H 4.57, N 19.51.

The synthetic route of 1122-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Garg, Gaurav; Pande, Milind; Agrawal, Ambika; Li, Jie; Kumar, Rakesh; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1771 – 1777;,
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