Category: pyrimidines

Reference of 330785-81-4, 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 330785-81-4, name is Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Ethyl 4-(3-chloro-4-methoxybenzylamino)-2-(methylthio)pyrimidine-5-carboxylate (200 mg, 0.59 mmol) was dissolved in dichloromethane (20 mL), m-CPBA (101 mg, 0.59 mmol) was added under ice-water bath, the reaction was heated to room temperature and conducted for 5 h. Water was added to the reaction and extracted with dichloromethane. The organic layer was dried, concentrated to obtain solid. The product was used in next reaction without any purification.

According to the analysis of related databases, 330785-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; XUANZHU PHARMA CO., LTD.; Shu, Chutian; Wu, Yongqian; (34 pag.)US2016/46654; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 29274-24-6 , The common heterocyclic compound, 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine, 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.

To a solution of 5-chloropyrazolo[1,5-a]pyrimidine (200 mg, 1.30 mmol) in DMF (2 mL) was added N-iodosuccinimide (322 mg, 1.86 mmol). The reaction was stirred at rt overnight, then diluted with EtOAc (100 mL), and washed with H2O (50 mL), saturated Na2S2O3 aqueous solution (50 mL) and brine (50 mL). The separated organic phase was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/PE (v/v)=1/4) to give the title compound as a pale yellow solid (390 mg, 100%). [0309] MS (ESI, pos. ion) m/z: 279.9 [M+H]+. [0310] 1H NMR (400 MHz, CDCl3) delta (ppm): 8.57 (d, J=7.2 Hz, 1H), 8.16 (s, 1H), 6.86 (d, J=7.2 Hz, 1H)

The synthetic route of 29274-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; Xi, Ning; US2014/234254; (2014); A1;,
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Synthetic Route of 3680-69-1, Adding some certain compound to certain chemical reactions, such as: 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H4ClN3, 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 3680-69-1.

In a 3L round bottom flask, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (92 g, 600 mmol) was suspended in 1600 mL dichloromethane; NBS (108 g, 600 mmol) was gradually added and the mixture was stirred at room temperature for 1 hr. An additional amount of NBS (20 g, 56 mmol) was added and the mixture was stirred at room temperature for 2 hours. The resulting solid was collected via filtration, rinsed with dichloromethane and dried. The solid was triturated with 2 L of water for 2 hours and the solid was collected via filtration; The solid was dried under a vacuum to a constant weight (112 g, 80%). 1H NMR (DMSO-de) delta 8.68 (s, 1H), 7.99 (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. 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIMERIX, INC.; ALMOND, Merrick; LANIER, Ernest, Randall; MUSSO, David, Lee; WARE, Roy; WO2010/135520; (2010); A1;,
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Synthetic Route of 171887-03-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 171887-03-9 as follows.

[0374] To a solution of 5 (20 g, 53 mmol) in n-BuOH (300 mL) was added DIPEA (28 mL) and 2-amino-4,6-dichloro-5-formamidopyrimidine (13.2 g, 64 mmol). Resulting mixture was heated in a sealed vessel at 160C for 24 h. Volatiles were evaporated, column chromatography (AcOEt in toluene 20-100%) afforded title compound (21 g, 75%) as a light yellow solid: 1H NMR (401 MHz, DMSO-d6) d 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) d 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,171887-03-9, its application will become more common.

Reference:
Patent; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY ASCR, V.V.I.; BIRKUS, Gabriel; DEJMEK, Milan; NENCKA, Radim; PAV, Ondrej; SALA, Michal; (206 pag.)WO2019/211799; (2019); A1;,
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Application of 4595-59-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4595-59-9 as follows.

General procedure: To a stirred solution of aryl halides (2.0 mmol) and thiourea (1.2 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 110 C for 15 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product in excellent yields.Recycling of the catalyst:after the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (2.0 mL) was added and CuO was removed by centrifugation. After each cycle, the catalyst was recovered by simple centrifugation, washing with deionized water and ethyl acetate and then drying in vacuo. The recovered nano CuO was used directly in the next cycle.Data of representative examples:Dip-tolylsulfane (Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Bis(4-ethylphenyl)sulfane (Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Bis(3-nitrophenyl)sulfane (Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.4,4′-Thiodianiline (Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Dithiophen-3-ylsulfane (Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Dipyrimidin-5-ylsulfane (Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; found: C, 50.45; H, 3.13; N, 29.41; S, 16.81.Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; f…

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Reference:
Article; Reddy, K. Harsha Vardhan; Reddy, V. Prakash; Shankar; Madhav; Anil Kumar; Nageswar; Tetrahedron Letters; vol. 52; 21; (2011); p. 2679 – 2682;,
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Application of 1722-12-9, 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 1722-12-9, name is 2-Chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 2-chloropyrimidines(10 mmol), potassium cyanide (13-15 mmol), water (20 mmol), and DMSO(20 mL) was heated to 60 C. A solution of 3-quinuclidinol (0.1-0.2 mmol) inDMSO(5 mL) was added to the reaction mixture over 0.5 h. The reaction mixturewas stirred at 50-70 C for additional hours as specified in Table 1. Uponcompletion, the mixture was cooled to room temperature and water (50 mL) wasadded. The resulting mixture was extracted with isopropyl acetate (3 40 mL)(product 7a precipitated out after water addition and was collected by filtration).The combined organic layers were washed with water (2 30 mL), dried overMgSO4, filtered, and concentrated under vacuum to give crude 2-cyanopyrimidines, which were purified by column chromatography (SiO2) to afford pureproducts.

According to the analysis of related databases, 1722-12-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Hong-Yong; Shieh, Wen-Chung; Prashad, Mahavir; Tetrahedron Letters; vol. 55; 36; (2014); p. 5055 – 5057;,
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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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., name: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

(A) 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5 g, 32.6 mmol) in THF (50 mL) was added NaH (30%, 4 g, 50.0 mmol) at 0 C. The reaction mixture was stirred at 0 C. for 1 hour before the addition of (2-(chloromethoxy)ethyl)-trimethylsilane (15 g, 90.0 mmol). The reaction was stirred at ambient temperature for 3 hours. It was then treated with water (5 mL) and extracted with EtOAc. The organic layer was concentrated under reduced pressure, and the residue was purified by chromatography to give the title compound. MS (m/z): 284 (M+H)+ (35Cl), 286 (M+H)+ (37Cl).

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, 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Su, Wei-Guo; Deng, Wei; Li, Jinshui; Ji, Jianguo; US2013/210831; (2013); A1;,
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Application of 1445-39-2, 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 1445-39-2, name is 2-Amino-5-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

2-Amino-5-iodopyrimidine (2.21 g), bis (triphenylphosphine) palladium dichloride (350 mg) and copper (I) iodide (40 mg) were stirred in DMF (100 mL)- triethylamine (20 mL) and degassed with nitrogen for 10 min. 3-Ethynyl aniline (1.29 g) was added and the mixture heated to 95 C for 2 hours. The solvent was evaporated and the residue was purified by trituration with DCM (20 mL) to give the title compound as a brown solid (1.25 g, 60%); ‘H NMR (DMSO-d6) 5.21 (bs, 2H), 6.58-6. 70 (m, 3H), 7.03-7. 07 (m, 3H), 8.40 (s, 2H); MS m/e MH+ 211.

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 1445-39-2, 2-Amino-5-iodopyrimidine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/60970; (2005); A1;,
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Reference of 89581-38-4 ,Some common heterocyclic compound, 89581-38-4, molecular formula is C6H5BrN2O2, 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 methyl 5-bromopyrimidine-2-carboxylate (2.30 g, 10.6 mmol) and copper (I) cyanide (1.92 g, 21.4 mmol) in a 100 mL round bottom flask was added DMA (21 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 5 min. The reaction mixture was heated to 110 C for 2 d and cooled to room temperature. The reaction mixture was diluted with EtOAc and water and filtered through a glass frit (medium). The filtrate was transferred to a separatory funnel. The aqueous phase was extracted with EtOAc (4 x) and the combined organic extracts were washed with brine (1 x), dried over MgSO4, filtered, concentrated to give a yellow oil. Purification by flash column chromatography on silica gel (80 g, 5% to 50% EtOAc in heptane) gave methyl 5-cyanopyrimidine-2-carboxylate (0.83 g, 5.08 mmol, 48% yield) as a white solid. LC/MS (ESI+) m/z = 164.0 (M+H).

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. 89581-38-4, Methyl 5-bromopyrimidine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); A1;,
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Related Products of 69034-12-4, 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.69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.531, as common compound, the synthetic route is as follows.

To a stirred solution of methyl-2-(2-fluorophenyl)-2-(4-(4,4,5,5-tetramethyl- l ,3,2-dioxaborolan-2-yl)phenyl)acetate (1.83 g, 4.8 mmol) in dioxane (80 mL) and water (20 mL) was added 2-chloro-5-trifluoromethylpyrimidine (1.0 g, 5.5 mmol) and K2C03 (1.35 g, 9.8 mmol). The mixture was degassed with N2 for 5 min, treated with Pd(PPh3)4 (280 mg, 0.24 mmol) and heated at 110 C overnight (LCMS indicated completion of the reaction). The mixture was cooled to r.t., treated with water (100 mL) and extracted with DCM (2 x 100 mL). The combined organic phase was separated, dried (MgS0 ), and evaporated in vacuo. Purification by chromatography (Si02) eluting with isohexane/ethyl acetate (95:5) afforded the subtitle compound as a white solid (1.45 g, 74% yield). LCMS (Rt 3.54 min, [M+H]+ 391). N.M.R. (CDC13) 9.01 (s, 2H), 8.48 (d, 2H, J = 8.4 Hz), 7.47 (d, 2H, J = 8.4 Hz), 7.30-7.25 (m, 2H), 7.13-7.05 (m, 2H), 5.38 (s, 1H), 3.78 (s, 3H).

Statistics shows that 69034-12-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-(trifluoromethyl)pyrimidine.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; MUNOZ-SANJUAN, Ignacio; BEAUMONT, Vahri; BECONI, Maria; BUeRLI, Roland, W.; HAUGHAN, Alan, F.; LUCKHURST, Christopher, A.; WALL, Michael; RAPHY, Gilles; THOMAS, Beth; WO2014/159210; (2014); A1;,
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