Tag: M.W:100-200

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4316-98-7, Adding some certain compound to certain chemical reactions, such as: 4316-98-7, name is 6-Chloro-4,5-diaminopyrimidine,molecular formula is C4H5ClN4, 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 4316-98-7.

6B. 6-Chloro-7,9-dihydropurin-8-oneA mixture of the 5,6-diamino-4-chloropyrimidine of Example 6A (1.0 g, 6.92 mmol) and N,N’-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1,4-dioxane (20 ml) was refluxed under argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86%) LC/MS (LCTl): Rt2.45 [M+H]+ 173, 171.

According to the analysis of related databases, 4316-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2007/125325; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 34171-40-9, Adding some certain compound to certain chemical reactions, such as: 34171-40-9, name is 2,4-Dichloro-5-ethylpyrimidine,molecular formula is C6H6Cl2N2, 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 34171-40-9.

To a mixture of 2-[[7-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indazol-1-yl]methoxy]ethyltrimethylsilane (2 g, 3.57 mmol) and 2,4-dichloro-5-ethylpyrimidine (947.53 mg, 5.36 mmol) in DME (25 mL) and H2O (5 mL) was added Pd(dppf)Cl2 (261.09 mg, 357.00 umol) and K2CO3 (986.33 mg, 7.14 mmol) in one portion at 20 C under N2. The mixture was stirred at 80 C for 2 h. The mixture was poured into water (100 mL) and extracted with EA (50 mL*2). The combined organic phase was washed with brine (100 mL*2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (PE/EA=100/1,40/1) to give 2-[[3-(2-chloro-5-ethylpyrimidin-4-yl)-7-fluoroindazol-1-yl]methoxy]ethyltrimethylsilane (600 mg, crude) as colorless oil. LCMS: M+H+: 407.1 1.087 min (5-95% ACN in H2O, 1.5 min).

According to the analysis of related databases, 34171-40-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MARINEAU, Jason, J.; ZAHLER, Robert; CIBLAT, Stephane; WINTER, Dana, K.; KABRO, Anzhelika; ROY, Stephanie; SCHMIDT, Darby; CHUAQUI, Claudio; MALOJCIC, Goran; PIRAS, Henri; WHITMORE, Kenneth, Matthew; LUND, Kate-Iyn; SINKO, Bill; SPROTT, Kevin; (418 pag.)WO2018/13867; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 7504-94-1, 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. 7504-94-1, name is 2-Hydrazinylpyrimidine. A new synthetic method of this compound is introduced below.

After adding 24 mg of 2-hydrazinopyrimidine and 0.030 ml of triethylamine to a 1 ml DMF solution containing 100 mg of {2-(3-hydroxymethyl-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (11e)), the mixture was stirred at 85 C. for 14 hours and 30 minutes under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 1 ml of methanol, 1 ml of THF and 0.050 ml of acetic acid. After adding 100 mg of sodium cyanotrihydroborate to the reaction mixture, it was stirred at room temperature for 21 hours and 30 minutes. The reaction mixture was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product. To a solution of the obtained crude product in 3 ml of a methanol:water:acetic acid=1:1:1 mixed solvent there was added 150 mg of iron powder, and the mixture was stirred at 60 C. for 17 hours under a nitrogen atmosphere. After filtering the reaction mixture, it was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give the title compound (28.50 mg). 1H-NMR (CD3OD) delta 1.95 (s, 3H) 3.78 (s, 3H) 4.58 (s, 2H) 5.68 (s, 1H) 6.87 (d, J=8.8 Hz, 2H) 6.91 (s, 1H) 7.03 (s, 1H) 7.13 (s, 1H) 7.35 (t, J=4.8 Hz, 1H) 7.61 (d, J=8.8 Hz, 2H) 8.78 (d, J=4.8 Hz, 2H) Mass spectrum (ESI) m/z: 447 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7504-94-1, 2-Hydrazinylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2008/15199; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1480-96-2, 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 1480-96-2 as follows.

43b2-Methoxy-5-fluorouracil (43a, 1.04g, 7.21 mmol) and N,N-dimethylaniline (1.80 mL) were heated in POCI3 at 11O0C for 90 minutes. After cooling, the reaction was added carefully to ice. The product was extracted with diethylether. The ether layer was washed with sequentially with 2N HCI, water, and brine followed by drying (MgSO4). The ether was carefully removed under reduced pressure to give 43b as a volatile liquid (0.39g, 34%) which was used without further purification. Rf = 0.26 (10% EtOAc/hexane). 1H NMR (400MHz, DMSO-d6): delta 3.91 (s, 3H), 8.79 (s, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1480-96-2, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2006/72831; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol, molecular formula is C4H6N4S, 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. Product Details of 1004-39-3

2~(pentylthio)-pyrimidine-4,6-diaminePyrimidine-4,6-diamine-2-thiol (10 g, 70.3 mmol) was dissolved in methanol (140 mL) at rt to which 70 mL of IN sodium hydroxide was added. This was followed by ?-pentyl bromide (8.5 mL, 1.1 eq) and 100 mL dimethylformamide. The reaction was then stirred at rt for 18 h. LC/MS indicated clean conversion to the desired product, and consumption of starting material. The reaction was then concentrated in vacuo to provide an oil. The crude reaction mixture was then diluted with water (200 mL) and extracted with dichloromethane (3 x 300 mL). The organic portions were combined and dried over sodium sulfate, filtered and concentrated in vacuo. The product was used without further purification; yield 14.8 g (69.7 mmol)

With the rapid development of chemical substances, we look forward to future research findings about 1004-39-3.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113538; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, 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, Recommanded Product: 3680-69-1, blongs to pyrimidines compound. Recommanded Product: 3680-69-1

To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.99 g, 26.0 mmol, 1.0 eq) in dry DCM(150 mL) under argon, N-bromosuccinimide (6.02 g, 33.8 mmol, 1.3 eq) was added and the resulting mixture was stirred at RT for 3 h. The reaction mixture was diluted with MeOH (30 mL) and then concentrated in vacuo to yield a slight brown solid. The residue was triturated with H20 (150 mL). The solid was collected by filtration and then re-crystallized in MeOH to afford 5-bromo-4-chloro-7H-pyrrolo[2,3-d] pyrimidine (4.0 g, 66% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12915; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia