Pyrimidines

Related Products of 883231-23-0, 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.883231-23-0, name is N-Boc-2-Amino-5-bromopyrimidine, molecular formula is C9H12BrN3O2, molecular weight is 274.11, as common compound, the synthetic route is as follows.

A mixture of tert-butyl (5-bromopyrimidin-2-yl) carbamate (17a) (360 mg, 0.96 mmol) , N, N-dimethylpiperidin-4-amine (246 mg, 1.92 mmol) , Pd2 (dba) 3 (44 mg, 0.048 mmol) , Xantphos (56 mg, 0.096 mmol) , t-BuONa (184 mg, 1.92 mmol) in toluene (11 mL) was heated at 110 for 18 h under N2. The mixture was cooled to room temperature and concentrated in vacco. The residue was purified by chromatography on silica gel eluting with DCM /MeOH (10: 1) to give tert-butyl (5- (4- (dimethylamino) piperidin-1-yl) pyrimidin-2-yl) carbamate (17b) . MS-ESI (m/z) : 322 [M + 1] +.

The chemical industry reduces the impact on the environment during synthesis 883231-23-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHONGQING FOCHON PHARMACEUTICAL CO., LTD.; SHANGHAI FOCHON PHARMACEUTICAL CO., LTD.; ZHAO, Xingdong; LI, Tongshuang; ZHANG, Huajie; LI, Zhifu; LIU, Bin; LIU, Qihong; TAN, Rui; RONG, Yue; YANG, Lijun; CHEN, Zhifang; TAN, Haohan; JIANG, Lihua; LIU, Yanxin; LINGHU, Li; LIN, Min; SUN, Jing; WANG, Weibo; (89 pag.)WO2017/114351; (2017); A1;,
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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. 22536-63-6, name is 2-Chloro-4-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. Recommanded Product: 22536-63-6

2-Bromopyridine or 2-chloropyrimidine (2equiv.), 5-amino-2-substitutedphenol (lequiv) and 37% HCl solution (2equiv) in 10% aqueous EtOH solution (0.2M) was stirred at 9O0C for 24h. The reaction mixture was diluted with AcOEt and washed with 5% aqueous K2CO3 solution and brine. The organic phase was dried over Na2SO4, concentrated and the crude product was purified by flash chromatography on silica gel.; Following the general procedure for the synthesis of 2-R-5-(heteroaryl-2-ylamino)phenol, 2- chloro-4-methoxypyrimidine (44 mg, 0.30 mmol) and 4-amino-o-cresol (37 mg, 0.30 mmol) in 10% aqueous EtOH (2 mL) was heated at 90 0C for 18h. The title compound was obtained in 21 % yield a (14 mg) and used for the next step without addittional purification. 1H NMR (500 MHz, CD3OD) £8.06 (d, J= 5.8 Hz, IH), 7.25 (d, J= 2.0 Hz, IH), 6.98 (d, J = 8.2 Hz, IH), 6.92 (dd, J= 8.2, 2.0 Hz, IH), 6.18 (d, J= 5.8 Hz, IH), 3.97 (s, 3H), 2.16 (s, 3H); 13C NMR (125 MHz, CD3OD) £ 172.1, 162.1, 159.1, 156.8, 140.3, 131.9, 120.2, 112.9, 108.5, 99.8, 54.5, 16.1.

With the rapid development of chemical substances, we look forward to future research findings about 22536-63-6.

Reference:
Patent; YALE UNIVERSITY; WO2007/38387; (2007); A2;,
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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. 10457-14-4, name is 2,4-Bis((trimethylsilyl)oxy)pyrimidine, molecular formula is C10H20N2O2Si2, 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. COA of Formula: C10H20N2O2Si2

A mixture of uracil (6.00 g, 53.53 mmol) and ammonium chloride (0.3 g, 5.60 mmol) in HMDS (15 ml) was refluxed for 10 h with the exclusion of moisture until a clear solution was obtained. The excess of silylating agent was removed under vacuum. The residual clear oil of 2,4-bis(trimethylsilyloxy)pyrimidine was dissolved in 25 ml of anhydrous 1,2-dichloroethane, and ethyl bromoacetate (5.92 ml, 53.53 mmol) was added. The reaction mixture was heated at reflux for 20 h, cooled to room temperature and treated with 15 ml of iPrOH. The resulting precipitate was collected and purified by flash chromatography eluting with 1:10 EtOH/1,2-dichloroethane to give 13 (9.45 g, 92%) as white crystals, mp 118-120 C, Rf 0.42 (EtOAc); 1H NMR (400 MHz, DMSO-d6) delta ppm 1.21 (3H, t, J = 7.1 Hz, CH3), 4.15 (2H, q, J = 7.1 Hz, CH2), 4.51 (2H, s, NCH2), 5.62 (1H, d, J = 7.8 Hz, H-5), 7.62 (1H, d, J = 7.8 Hz, H-6), 11.40 (1H, br s, H-3); 13C NMR (100 MHz, DMSO-d6) delta ppm 14.0, 39.1, 39.3, 39.5, 39.7, 39.9, 48.6, 61.2, 101.1, 145.9, 151.0, 163.8, 168.2.

With the rapid development of chemical substances, we look forward to future research findings about 10457-14-4.

Reference:
Article; Babkov, Denis A.; Valuev-Elliston, Vladimir T.; Paramonova, Maria P.; Ozerov, Alexander A.; Ivanov, Alexander V.; Chizhov, Alexander O.; Khandazhinskaya, Anastasia L.; Kochetkov, Sergey N.; Balzarini, Jan; Daelemans, Dirk; Pannecouque, Christophe; Seley-Radtke, Katherine L.; Novikov, Mikhail S.; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 1069 – 1081;,
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Reference of 56686-16-9, 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 56686-16-9 as follows.

t-BuLi (Aldrich; 1.7 M soln in pentane, 1.1 mL) was added to a mixture of 8 (Aldrich; 200 mg, 0.9 mmol) and dry THF (2 mL) at -78 C under argon. The mixture was left at -78 C for 30 min and then compound 3 (190 mg, 0.8 mmol) was added. The mixture was allowed to warm to room temperature. The reaction was followed by TLC (CHCl3/acetone, 85/15, v/v) at 30 min intervals. After stirring for 3 h at room temperature, when 3 was no longer detected by TLC, Et2O (20 mL) was added. The mixture was washed with H2O (5 mL) and evaporated to dryness. The residue was dissolved in 1,4-dioxane (6 mL) and CH2Cl2 (2 mL). Cu(OAc)2 (40 mg), NH3 (aq) (0.3 mL) and H2O (1 mL) were added. The mixture was stirred at room temperature for 1 d. The organic layer was separated, washed with H2O (10 mL), dried (MgSO4) and concentrated to dryness. Column chromatography of the residue (CHCl3/acetone, 85/15, v/v) gave 9 (70 mg, 39%), 10 (89 mg, 71%), and 11 (50 mg, 17%). 9: A white solid (mp >180 C, dec). deltaH (CDCl3, 200 MHz) 1.43-1.56 (16H, m), 1.90 (4H, m), 2.35 (4H, m), 3.29 (4H, m), 3.56 and 4.34 (8H, AB quartet, 2JAB 11.4 Hz); deltaC (CDCl3, 50 MHz) 22.34, 22.58, 25.42, 26.16, 27.48, 28.49, 36.98, 64.28, 66.43, 72.57, 98.80, 136.38; numax (KBr) 2936, 2860, 1496, 1448, 1380, 1240, 1156, 1044, 920; HRMS (EI, 70 eV) m/z calcd for C24H36O6N2 (M+) 448.2573, found 448.2557. 11: A white solid (mp 151-152 C). deltaH (CDCl3, 200 MHz) 1.34-1.84 (8H, m), 2.1 (2H, m), 2.39 (2H, m), 3.12 (2H, m), 3.63 and 4.57 (4H, AB quartet, 2JAB 11.4), 4.00 (3H, s), 4.02 (3H, s), 10.09 (1H, s); deltaC (CDCl3, 50 MHz) 22.39, 22.67, 25.49, 27.42, 28.21, 28.84, 37.29, 54.21, 55.19, 64.36, 72.23, 98.77, 105.98, 136.72, 159.26, 165.04, 167.74; numax (KBr) 2948, 2936, 1716, 1688, 1556, 1536, 1480, 1464, 1356, 1252, 1244, 1108; HRMS (EI, 70 eV) m/z calcd for C18H25O5N3 (M+) 363.1794, found 363.1812. The NMR spectra of 10 were consistent with those described: H. Pelissier, J. Rodriguez and K.P.C. Volhardt, Chem. Eur. J. 5 (1999), p. 3549. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (27)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56686-16-9, its application will become more common.

Reference:
Article; Koszytkowska-Stawi?ska, Mariola; Mironiuk-Puchalska, Ewa; Sas, Wojciech; Tetrahedron Letters; vol. 52; 16; (2011); p. 1866 – 1870;,
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Reference of 3177-24-0, 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 3177-24-0 as follows.

To a cooled (-60 °C) solution of (lr,4r)-4-ethoxycyclohexanamine (6.82 g, 37.9 mmol) and 2,4-dichloropyrimidine-5-carbonitrile (6 g, 34.5 mmol) in THF (115 mL) was added DIEA (15.02 mL, 86 mmol) dropwise. The resulting mixture was stirred at -60 °C for 1 h and then allowed to warm to room temperature overnight. The resulting mixture was concentrated and the residue was purified by silica gel column- 125 -ATI-2514175vl chromatography (14 percent ethyl acetate in petroleum ether). The product fractions were combined and concentrated to afford 2-chloro-4-((lr,4r)-4-ethoxycyclohexylamino)- pyrimidine-5-carbonitrile (3.33 g, 11.86 mmol, 34.4 percent yield) and 4-chloro-2-((lr,4r)-4- ethoxycyclohexylamino)pyrimidine-5-carbonitrile (5.5 g, 19.59 mmol, 56.8 percent yield;1H NMR (400 MHz, DMSO-d6) delta ppm 8.62 – 8.87 (m, 2 H), 3.61 – 3.86 (m, 1 H), 3.44 (dd, J=7.03, 2.34 Hz, 2 H), 3.12 – 3.26 (m, 1 H), 1.75 – 2.15 (m, 4 H), 1.13 – 1.44 (m, 4 H), 1.08 (td, J=6.93, 1.76 Hz, 3 H); MS (ESI) m/z 281.1 [M+l]+) as white solids. Theregiochemistry of the major isomer was confirmed by comparison with the proton spectra of 4-chloro-2-((lr,4r)-4-methoxycyclohexylamino)pyrimidine-5-carbonitrile (synthesis described herein).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
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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. 1005-38-5, name is 4-Amino-6-chloro-2-(methylthio)pyrimidine, molecular formula is C5H6ClN3S, 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. Quality Control of 4-Amino-6-chloro-2-(methylthio)pyrimidine

EXAMPLE 124 3-[4-(3,5-Dichloropyrid-4-ylcarboxamido)phenyl]-2-[4-chloro-2-(methylthio)pyrimidin-6-yl amino]propanoic acid 6-Amino-4-chloro-2-(methylthio)pyrimidine gave the title compound (1.4mg) HPLC-MS Retention time 2.63 min; MH+ 512.

With the rapid development of chemical substances, we look forward to future research findings about 1005-38-5.

Reference:
Patent; Celltech Therapeutics Limited; US6348463; (2002); B1;,
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Electric Literature of 4316-97-6 ,Some common heterocyclic compound, 4316-97-6, molecular formula is C5H4Cl2N2, 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-dichloro-5-methylpyrimidine (0.98 g, 6.0 mmol), 4-chloro-2-methylphenylboronic acid (2.24 g, 13 . 2 mmol), acetonitrile (100 ml) and 1 M sodium carbonate (Na 2 CO 3) (30 ml), and nitrogen bubbling was carried out for 1 hour.Thereafter, 2210 mg of PdCl 2 (PPh 3), 0.3 mmol) was added and the reaction was carried out under reflux. The reaction solution was a yellow clear solution. Disappearance of the raw material was confirmed by TLC after 3 hours.After a while, since an orange solid precipitated, suction filtration was carried out, after washing with methanol, the filtrate was dissolved in chloroform. Washed with water 150 ml × 3 times, brine 150 ml × 1 time, and evaporation was carried out. In order to remove the catalyst, silica gel column chromatography was carried out. A glass filter 17G-4 was used and 150 cc of silica gel was used.The injection solvent was toluene, and the developing solvent was hexane: ethyl acetate = 10: 3 (vol / vol). After the evaporation, 1.0 g of a white solid was obtained, and the yield was 49%. From 1 H-NMR and MS, it was confirmed that 3 MHPM-Cl (molecular weight 343) was formed.

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. 4316-97-6, 4,6-Dichloro-5-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; YAMAGATA UNIVERSITY; SASABE, HISAHIRO; KIDO, JUNJI; KOMATSU, RYUTARO; NAKAO, KOHEI; (58 pag.)JP2018/35129; (2018); A;,
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Related Products of 4316-97-6, 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. 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine. A new synthetic method of this compound is introduced below.

1 -(6-Chloro-5-methylpyrimidin-4-yl)-2,3-dihvdro-1 H-imidazon ,2- blpyrazoleTo a solution of 2,3-dihydro-1 H-imidazo[1 ,2-b]pyrazole (Preparation 12) (14.1 g, 129 mmol) and 4,6-dichloro-5-methylpyrimidine (21.1 g, 129 mmol) in 800 mL of tetrahydrofuran cooled down to zero degrees Celsius was added sodium bis(trimethylsilyl)amide (1 M in tetrahydrofuran, 138 ml_, 138 mmol) drop-wise over 1 hour. After 2 hours, water was added and tetrahydrofuran evaporated. Dichloromethane was then added and the aqueous phase was extracted 3 times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was dissolved in a minimum amount of dichloromethane and the desired product was precipitated using heptane. The resulting solid was filtered, washed with heptane and dried under vacuum to give 24.6g (90% yield) of a beige solid. LCMS (ES+): 236.3 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4316-97-6, its application will become more common.

Reference:
Patent; PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton; WO2011/61679; (2011); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, the common compound, a new synthetic route is introduced below. Safety of 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde

4,6-Dichloropyrimidine-5-acetaldehyde 1 (2.0 g, 10.5 mmol) dissolved in 80 mLEthanol, adding triethylamine (3.0 mL,21.06 mmol), stirred at room temperature for 10 min.Then tert-butylamine (2.2 mL, 21.06 mmol) was added to the mixture, and the reaction solution wasAfter stirring at 90 C for 6 h, the reaction was monitored by TLC. After the reaction is completed, after evaporating the solvent,The crude reaction product was dissolved in dichloromethane/water.(volume ratio = 1:1) 100 ml × 3 times.Separation and purification by column chromatography to obtain a white solid1.0 g (yield 55.2%).

The synthetic route of 16019-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University Huaxi Hospital; He Yang; Chai Yingying; Li Weimin; Zhou Xinglong; (20 pag.)CN108794483; (2018); A;,
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Application of 851984-15-1 , The common heterocyclic compound, 851984-15-1, name is 6-Chloro-5-fluoropyrimidin-4-amine, molecular formula is C4H3ClFN3, 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 the Boc protected amine 31.15 (1 eq) was in 1 ,4-dioxane (50 eq) was added HC1 (4 N in 1 ,4 dioxane 15 eq) and the solution was heated to 60 oC for 60 min. The solvent was removed in vacuo and the crude amine (1.0 eq) was dissolved in 1 -butanol (100 eq) and treated with 6-chloro-5-fluoropyrimidin-4- amine (1.5 eq) and DIPEA (10.0 eq). The reaction solution was stirred at 1 10 C for 16 h, cooled to rt and diluted with EtOAc (20 mL), washed with H20 (10 mL), saturated brine (10 mL), dried ( a2S04), filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (Petroleum ether/EtOAc 1/1) to give the desired product compound 279 as light yellow solid (63% yield).1.. NMR (400 MHz, CDC13) delta 7.93 (br. s., 1H), 6.44 (br. s., 1H), 6.39 (br. s., 1H), 6.23 (br. s., 1H), 4.71 (m, 1H), 4.01 (m, 1H), 3.82 (m, 1H), 3.40 (br. s., 1H), 3.17 – 3.23 (m, 1), 2.47 (br. s., 1H), 2.35 (s, 2H), 2.35 (m, 1H), 2.03 (br. s., 2H), 1.60 (br. s., 1H). EIMS (m/z): calcd. for C2oH22ClF3 60 (M+) 454.8, found 454.8.

The synthetic route of 851984-15-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC.; ERLANSON, Daniel, A.; MARCOTTE, Doug; KUMARAVEL, Gnanasambandam; FAN, Junfa; WANG, Deping; CUERVO, Julio, H.; SILVIAN, Laura; POWELL, Noel; BUI, Minna; HOPKINS, Brian, T.; TAVERAS, Art; GUAN, Bing; CONLON, Patrick; ZHONG, Min; JENKINS, Tracy, J.; SCOTT, Daniel; SUNESIS PHARMACEUTICALS, INC.; LUGOVSKOY, Alexey, A.; WO2011/29046; (2011); A1;,
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