Pyrimidines

Related Products of 36314-97-3 ,Some common heterocyclic compound, 36314-97-3, molecular formula is C10H8ClN3, 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.

Compound 1e (13 g, 7.34 mmol) was dissolved in 300 mL of N,N-dimethylformamide and N-bromosuccinimide (12.38 g, 69.54 mmol) was added, and the reaction was stirred for 1 hour. The reaction was stopped, the reaction solution was poured into 1 L of water, stirred for 20 minutes, filtered, and the filter cake was dried.The crude title compound 2a (18 g) was obtained, which was used for the next step without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,36314-97-3, its application will become more common.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Lu Biao; Wang Shenglan; Shen Xiaodong; He Feng; Tao Weikang; (56 pag.)CN109535161; (2019); A;,
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Electric Literature of 61044-96-0, 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 61044-96-0, name is 4-Chloro-5-methyl-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A microwave vial is charged with 4-chloro-5-methyl-2-methylsulfanylpyrimidine (174 mg, 1 mmol), 10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione (166 mg, 1 mmol), palladium acetate (12 mg, 0.05 mmol), X-Phos (48 mg, 0.1 mmol) and potassium phosphate (424 mg, 2 mmol). 1 ,2-dimethoxyethane (3 ml) is added and the reaction heated to 160 0C, with stirring, for 30 minutes. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 4-(5-methyl-2-methylsulfanyl-pyrimidin-4-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5- dione (34 mg).

According to the analysis of related databases, 61044-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA LIMITED; WO2009/30450; (2009); A2;,
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Synthetic Route of 65996-58-9, 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.65996-58-9, name is 2-Amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one, molecular formula is C6H6N4O, molecular weight is 150.14, as common compound, the synthetic route is as follows.

To a suspension of 2-amino-SH-pyrrolo [3, [2-D] PYRIMIDIN-4 (3H)-ONE] (9- deazaguanine) (0.454 g, 3.0 mmol) (prepared according to J. Org. Chem. 1978,43, 2536) and 2-O-methyl-1, 3, [5-TRI-O-BENZOYL-D-D-RIBOFURANOSE] (1.54 g, 3.2 mmol) in dry nitromethane (23 mL) at [60C] was added stannic chloride (0.54 mL, 4.5 mmol). The reaction mixture was maintained at this temperature for 0.5 hr. , cooled and poured onto ice-cold saturated sodium bicarbonate solution (70 mL). The insoluble material was filtered through florisil and washed with ethyl acetate [(3X50] mL). The filtrate was extracted with ethyl acetate [(2X50] mL), and organic layer was washed with water [(2X50] mL), dried over [NA2SO4] and evaporated to dryness. Chromatography of the resulting foam on silica gel with [CH2CI2/MEOH] (14: 1) afforded the benzoylated product (0.419 g, 30% yield). To a suspension of the benzoylated product (0.25 g) in MeOH (2.4 mL) was added t-butylamine (0.52 [ML)] and stirring at room temperature was continued for 24 hrs. followed by addition of more t-butylamine [(0. 2] mL). The reaction mixture was stirred at ambient temperature overnight, concentrated in vacuum and the residue was purified by flash chromatography over silica gel using CH2Cl2/MeOH (85: 15) as eluent giving the desired compound as a foam (0.80 g). ‘H NMR [(200MHZ,] [DMSO-D6)] : [3] Hz3.28 (s, 3H), 3.40-3. 52 (m, 3H), 3.87-3. 90 (m, 1H), 4.08-4. 09 (m, 1H), 4.67 (d, 1H, J = 5.2 Hz), 4.74 (d, 1H, J = 7.0 Hz), 5.62 and 5.50 (2 bs, 3H), 7.14 (d, 1H, [J=] 2.6 Hz), 10.43 (s, [LH),] 11.38 (s, [LH)] ; Mass spectrum: calcd. for C12H16N4O5: 296. 28; found: 295.11.

The chemical industry reduces the impact on the environment during synthesis 65996-58-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ISIS PHARMACEUTICALS, INC.; WO2003/99840; (2003); A1;,
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Related Products of 144927-57-1, 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.144927-57-1, name is Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, molecular formula is C9H8ClN3O2, molecular weight is 225.6317, as common compound, the synthetic route is as follows.

Ethyl 4-chloro-7H-pyrrolo[2,3-^pyrimidine-5-carboxylate (50.0 mg, 0.222 mmol), phenyl boronic acid (32.4 mg, 0.266 mmol) and potassium carbonate (0.332 mL, 0.665 mmol) were added to tetrahydrofuran (1.5 mL) in a microwave vial. The solution was purged with nitrogen for 5 minutes and PdCl2(dppf)-CH2Cl2 (18 mg, 0.022 mmol) was then added. The reaction was sealed and heated at 125 C by microwave irradiation for 30 minutes. The reaction mixture was diluted with EtOAc and washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification of desired product was carried out by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. Pure fractions were pooled and concentrated under reduced pressure. Saturated aqueous sodium bicarbonate and EtOAc were added to the residue. The organic layer was separated and the aqueous layer was then extracted with EtOAc (x3). The combined organic layers were then washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the product as a solid. LRMS (ESI) calc’d for C15Hi4ClN302 [M+H]+: 268, found268. 1H NMR (600 MHz, DMSO-D6) delta 13.01 (s, 1H), 8.91 (s, 1H), 8.30 (s, 1H), 7.63 (m, 2H), 7.49 (m, 3H), 3.82 (q, 2H, J= 7.04 Hz), 0.78 (t, 3H, J= 7.04 Hz).

The chemical industry reduces the impact on the environment during synthesis 144927-57-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
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Application of 10132-07-7 ,Some common heterocyclic compound, 10132-07-7, molecular formula is C4H3Cl2N3, 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.

A solution of 3-cyanobenzylaldehyde (1.0 g) and N-cyclohexyl-1,3-propane-diamine (2.4 g) in CH3OH (150 mL) was heated to 60 C. for 18 hours. After cooling to room temperature, NaBH4 (1.5 g) was slowly added to the above solution. The mixture was stirred for another 30 minutes. The mixture was then concentrated, quenched with NH4Cl (aq), and extracted with CH2Cl2. The organic layers were combined, dried with anhydrous MgSO4, and concentrated to give a residue. The residue was purified by chromatography on silica gel (EtOAc/Et3N=7/3) to afford Intermediate 201-I (1.6 g) in a 80% yield. A solution of Intermediate 201-I (1.6 g) and Boc2O (3.5 g) in CH2Cl2 (160 ml) was stirred at 25 C. for 15 hours and then concentrated. The resultant residue was purified by chromatography on silica gel (EtOAc/Hexane=1/1) to afford Intermediate 201-II as a yellow oil (2.36 g) in a 85% yield. A solution of Intermediate 201-II and LiAlH4 (2.3 g) in THF (230 mL) was stirred at 0 C. for 4 hours. After Na2SO4110H2O was added, the solution was stirred at room temperature for 0.5 hour. The solution was then filtered through a celite pad. The filtrate was dried over anhydrous MgSO4 and concentrated to give a residue. The residue was purified by column chromatography on silica gel (using MeOH as an eluant) to afford Intermediate 201-III (1.1 g) in a 50% yield. Diisopropylethylamine (1.1 mL) was added to a solution of 2,4-dichloro-6-aminopiperidine (0.41 g) and Intermediate 201-III (1.1 g) in 1-pentanol (10 mL). The reaction mixture was stirred overnight at 120 C. The solvent was removed under vacuum and the residue was purified by column chromatography on silica gel (EtOAc/Hexane=3/7) to afford 201-IV (1.0 g) in a 65% yield. To a solution of Intermediate 201-IV (1.0 g) in 1-pentanol (1 mL) was added N1-hydroxyethoxyethyl piperazine (0.25 g). After the solution was stirred at 120 C. for 8 hours, it was concentrated. The residue thus obtained was purified by column chromatography on silica gel (EtOAc/MeOH=4/1) to afford Intermediate 201-V (730 mg) in a 60% yield. A solution of 20% TFA/CH2Cl2 (5 mL) was added to a solution of Intermediate 201-V (0.73 g) in CH2Cl2 (2 mL). The reaction mixture was stirred for 5 hours at room temperature and concentrated by removing the solvent. The resultant residue was purified by column chromatography on silica gel (21% NH3 (aq)/MeOH=1/19) to afford Compound 201 (434 mg) in a 85% yield. Compound 201 was then treated with 1 M HCl (4 mL) in CH2Cl2 (2 mL) for 0.5 hour. After the solvents were removed, the residue was treated with ether and filtered to give hydrochloride salt of compound 201. CI-MS (M++1): 541.3.

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. 10132-07-7, 4-Amino-2,6-dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yen, Chi-Feng; Hu, Cheng-Kung; Chou, Ming-Chen; Tseng, Chen-Tso; Wu, Chien-Huang; Huang, Ying-Huey; Chen, Shu-Jen; King, Chi-Hsin Richard; US2006/281712; (2006); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 22536-61-4, 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 22536-61-4, name is 2-Chloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

[0409j (E)-5-methyl-2-(prop-1-en-1-yl)pyrimidine, Example 14.01. To a 500 mL round bottomed flask was added 2-chloro-5-methylpyrimidine (12 g, 93 mmol), potassium (E)-trifluoro(prop-1-en-1-yl)borate (17.27 g, 117 mmol), and potassium phosphate (59.4 g, 280 mmol). The flask was purged with N2 (5x) and then 1,4-dioxane (200 mL) and water (20 mL) were added. The resulting yellow suspension was bubbled with Ar for 15 mm and then 1,1 -bis [(di-t-butyl-p-methylaminophenyljpalladium(II) chloride (Amphos, commercially avaliable from Strem, 2.64 g, 3.73 mmol) was added, a reflux condenser was attached and the reaction warmed to 90 C in an oil bath and stirred under N2 for 16.5 h. The reaction was then cooled to RT. The reaction was diluted with water (250 mL), and extracted with EtOAc (2 x 250 mL). The organic layers were combined, dried (MgSO4), and concentrated. The residue was purified by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes) to afford (E)-5-methyl- 2-(prop-1-en-1-yl)pyrimidine 14.01 (12.96 g, 97 mmol, 100% yield) as a yellow/orange oily solid. ?H NMR (300 MHz, CDC13) = 8.49 (s, 2H), 7.0 1-7.20 (m, 1H), 6.57 (dd, J= 15.6, 1.7 Hz, 1H), 2.29 (s, 3H), 1.97 (dd, J= 6.8, 1.6 Hz, 3H). MS (ESI pos. ion) m/z:(M–H).

According to the analysis of related databases, 22536-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
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Related Products of 35265-82-8, 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 35265-82-8, name is 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2,4-dichloro-6-methylthieno[3,2-d]pyrimidine (450 mg, 2.05 mmol), aqueous NaOH (1N, 4 mL) and THF (4 mL) was stirred at room temperature under N2. The reaction was monitored by HPLC until the reaction was completed. Then the mixture was neutralized to PH 5 by addition of 2N aqueous HCl. The solid was filtrated and dried to give 380 mg of 2-chloro-6-methylthieno[3,2-d]pyrimidin-4(3H)-one (yield was 92%) as a yellow solid. MS obsd. (ESI+) [(M+H)+]: 201.

According to the analysis of related databases, 35265-82-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc; Liang, Chungen; Wang, Lisha; Yun, Hongying; Zheng, Xiufang; US2013/90328; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90905-32-1, 2-Methoxypyrimidine-5-carbaldehyde, 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, Product Details of 90905-32-1, blongs to pyrimidines compound. Product Details of 90905-32-1

To a stirred solution of 4-bromothiazole (50.0 mg, 0.3 05 mmol) in THF (2 mL) under nitrogen atmosphere was added n-butyllithium (2.5 molar solution in hexane) (0.183 mL, 0.45 7 mmol) at – 78 C. Resulting pale yellow solution was stirred at -78 C for 30 mm. Then, 2- methoxypyrimidine-5-carbaldehyde (37.9 mg, 0.274 mmol) in 0.5 mL THF was added and the reaction mixture was stirred at -78 C for 1 h. Reaction was quenched with water (2 mL) anddiluted with ethyl acetate (5 mL). The organic layer was separated, washed with brine, dried over anhydrous sodium sulphate and evaporated under vacuum to get the crude product. The crude product was purified by combiflash chromatography (4 g Redisep Si02 column, eluting with 72% EtOAc in n-hexanes) to afford the title compound 143A (30 mg, 32%) as a pale yellow oil. LC-MS retention time = 0.84 mm; m/z = 304.0 [M+Hf AQUITY UPLC BEH C18 (3.0 x 50mm)1.7 micron column; Mobile Phase A: 5 mM ammonium acetate in 95% Water/ 5% ACN; Mobile Phase B: 5 mM ammonium acetate in 5% Water/ 95% ACN; Gradient time 1.7 mm. 20% B to 90% B over 1.7 mm. Flow rate 0.7 mL/min; Detection: UV at 220 nm. 1H NMR (400 MHz, CD3OD) oe ppm 8.63 (s, 2H), 7.55 (s, 1H), 6.05 (s, 1H), 4.03 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90905-32-1, 2-Methoxypyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; DEVASTHALE, Pratik; YE, Xiang-Yang; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; BALASUBRAMANIAN, Palanikumar; GUERNON, Leatte R.; CIVIELLO, Rita; HAN, Xiaojun; PARKER, Michael F.; JACUTIN-PORTE, Swanee E.; (290 pag.)WO2018/89353; (2018); A1;,
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Application of 425394-89-4 , The common heterocyclic compound, 425394-89-4, name is 4,6-Dichloropyrimidin-5-ol, molecular formula is C4H2Cl2N2O, 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 No.31 4-(hydroxymethyl)cyclohexan-1-ol (0.237 g, 1.82 mmol) in No.13 THF (15 mL) was added No.23 triphenylphosphine (0.718 g, 2.74 mmol) and No.23 4,6-Dichloropyrimidin-5-ol (0.3 g, 1.82 mmol). To the mixture was added No.31 di-tert-butyl azodicarboxylate (0.63 g, 2.74 mmol) at 0C., the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 as eluent) to afford the 4-(((4,6-dichloropyrimidin-5-yl)oxy)methyl)cyclohexan-1-ol (0.15 g, 30% yield). LC/MS APCI: Calculated 276.04; Observed m/z [M+H)]+ 277.0.

The synthetic route of 425394-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arrien Pharmaceuticals LLC; Vankayalapati, Hariprasad; US2020/131154; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13036-57-2, 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. 13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, 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 solution of 2-chloro-4-methylpyrimidine (Ig5 7.78mmol) and zinc cyanide (475mg, 4.04mmo) in anhydrous DMF (10ml) was added Pd(PPh3)4 (449mg, 0.366mmol) and nitrogen flushed through the mixture for 5 min. The mixture was heated at 180C for 30 min in a microwave reactor. The reaction was repeated on the same scale and the reaction mixtures were combined. The mixture was partitioned between EtOAc and water (filtered through celite to remove some insolubles), and the organic layer washed with sat. NaCl5 dried over MgStheta4, filtered and evaporated. The residue was purified by MPLC (Biotage Horizon; FLASH 25+M) eluent: 100% Hexanes (90ml), gradient rising from 100% Hexanes to 15% EtOAc in Hexanes (900ml), then 15% EtOAc in Hexanes (500ml) to give Ig of the title compound (54%) as an off- white solid. 1H NMR (CDCl3): 2.62 (s, 3H), 7.42 (d, J 5.1 Hz, 1H)5 8.69 (d, J 5.1 Hz, 1H).

According to the analysis of related databases, 13036-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; EDMONDSON, Scott, D.; CHANG, Lehua; KAR, Nam Fung; MORRIELLO, Gregori, J.; MOYES, Christopher, J.; SHEN, Dong-Ming; ZHU, Cheng; ANTHONY, Neville, J.; JONES, Philip; SMITH, Graham, F.; SCOTT, Mark, E.; THOMPSON, Christopher, F.; JUNG, Joon; CAMMARANO, Carolyn; HOFFMAN, Dawn Marie; WO2011/25774; (2011); A1;,
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