Day: August 10, 2021

Electric Literature of 99420-75-4 ,Some common heterocyclic compound, 99420-75-4, molecular formula is C6H6N2O2, 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-methylpyrimidine-2-carboxylic acid (1 g, 7.24 mmol) in DMF (72.4 ml) was added 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24mmol), and N,0- dimethylhydroxylamine hydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to 0 C and 1-propanephosphonic acid cyclic anhydride, 50 wt. % solution in EtOAc (9.21 ml, 14.48 mmol) was added droppwise. The mixture was allowed to warm to RT overnight. LCMS indicated complete conversion to product. The mixture was diluted with water, extracted with CHC13:IPA (3: 1) and washed with brine and NaHC03. The mixture was dried over Na2S04, concentrated in vacuo and purified by silica gel chromatography (0-100% heptane s:EtO Ac) to yield N-methoxy-N,5-dimethylpyrimidine- 2-carboxamide (0.7 g, 3.86 mmol, 53.4 % yield). NMR (500 MHz, CDC13) delta 8.61 – 8.69 (m, 2 H) 3.61 – 3.79 (m, 3 H) 3.27 – 3.47 (m, 3 H) 2.34 – 2.45 (m, 3 H). LCMS-ESI (pos.) m +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99420-75-4, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; SHARMA, Ankit; (321 pag.)WO2018/93576; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, 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: 26032-72-4, blongs to pyrimidines compound. Recommanded Product: 26032-72-4

Step (i): Synthesis of (2-chloro-6-phenyl-pyrimidin-4-yl)-((R)-1-phenyl-ethyl)-amine To 2,4-dichloro-6-phenylpyrimidine (1.343 g, 6 mmol), dissolved in 30 mL methanol, was added DIEA (1.1 mL, 6 mmol) and was stirred for 23 min at about 20-35 C. under a nitrogen atmosphere. To this mixture was added (R)-(+)-alpha-methyl-benzylamine (0.76 mL, 6 mmol) and stirred for about 10-19 h. The mixture was concentrated by rotary evaporation and purification (Biotage Horizon HPFC system chromatography, SiO2, 20:80 EtOAc: hexane) gave the title compound as a white solid (570 mg, 30.8% yield).1H NMR (300 MHz, CDCl3, TMS): delta 7.81-7.90 (m, 2H), 7.46-7.25 (m, 8H), 6.43 (s, 1H), 5.57 (s, 1H), 4.88 (s, 1H), 1.60 (d, J=6.6 Hz, 3H).LC-MSD (ES+): m/z [310 (M+H)+, 100].

The synthetic route of 26032-72-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144722; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 56844-12-3, 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 56844-12-3 as follows.

[0123] To diisopropylamine (1.028 ml, 7.21 mmol, 1.8 equiv) in 10 mL THF at 0 C was added n-butyl lithium (3.76 ml, 6.01 mmol, 1.5 equiv). After 1 h, the LDA solution was transferred to a solution of 6-bromo-4-chlorothieno[2,3-d]pyrimidine (1.0 g, 4.01 mmol, 1.0 equiv) in 35 mL THF at -78 C under nitrogen. The solution stirred for 1 h at -78 C after which a mixture of 1.25 mL water and 5 mL THF was added slowly. The mixture was then warmed to 0 C, poured into 60 mL water, and extracted with dichloromethane. The combined organic extracts were then dried over Na2SC> , filtered, and concentrated in vacuo to give a yellow solid which was chromatographed with 20% EtOAc/Hexanes gradient elution to give 5-bromo-4-chlorothieno[2,3-d]pyrimidine (671 mg, 67.1 % yield) as a tan solid. NMR (400 MHz, chloroform- ) delta ppm 8.85 (s, 1 H), 7.64 (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,56844-12-3, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; MARUGAN, Juan, J.; ZHENG, Wei; SOUTHALL, Noel; HUANG, Wenwei; MCCOY, Joshua, G.; TITUS, Steven; PATNAIK, Samarjit; WO2012/44993; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 62802-38-4, name is 5-Bromo-2-fluoropyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 62802-38-4

To a solution of 5-bromo-2-fluoro-pyrimidine (1.0 g, 4.93 mmol) and 6,7- dihydro-5H-pyrrolo[l,2-a]imidazol-2-amine (0.87 g, 4.93 mmol) in DMSO (20 mL) was added DIEA (1.27 g, 9.86 mmol), and the mixture was stirred at 100 C for 2 h under 2 before it was allowed to cool to rt. The mixture was purified by reverse phase column chromatography (Welch Ultimate XB-C18, 40-70 muiotaeta) eluting with a gradient of 20-95% acetonitrile in water to afford N-(5-bromopyrimidin-2-yl)-6,7-dihydro-5H-pyrrolo[l,2- ]imidazol-2-amine.

The synthetic route of 62802-38-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PLEXXIKON INC.; HOLLADAY, Mark W.; LIU, Gang; (267 pag.)WO2017/19804; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 573675-31-7 ,Some common heterocyclic compound, 573675-31-7, molecular formula is C7H3BrClN3, 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.

Step 1: 7-bromo-N-(2-methylbiphenyl-3-yl)pyrido[3,2-d]pyrimidin-4-amine To a vial was added 2-methylbiphenyl-3-amine (Example 1, Step 1: 0.4 g, 2.18 mmol), 7-bromo-4-chloropyrido[3,2-d]pyrimidine (Ark Pharm, cat#AK-27560: 540 mg, 2.2 mmol), and isopropyl alcohol (10. mL) The mixture was heated to 110 C. for 4 h. The mixture was cooled to room temperature, concentrated, and the crude product was used directly in the next step without further purification. LC-MS calculated for C20H16BrN4 (M+1)+: m/z=391.1; found 391.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,573675-31-7, its application will become more common.

Reference:
Patent; Incyte Corporation; Lajkiewicz, Neil; Wu, Liangxing; Yao, Wenqing; (58 pag.)US2017/174679; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 187035-79-6, Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate, 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 187035-79-6, blongs to pyrimidines compound. Product Details of 187035-79-6

Example 13 (R)-(2-(8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)-4-(trifluoromethyl)pyrimidin-5-yl)methanol and (S)-(2-(8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)-4-(trifluoromethyl)pyrimidin-5-yl)methanol To a solution of (R)-methyl 1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (80 mg, 0.228 mmol) in iPrOH (2 mL) and DCM (1 mL) was added ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate (174 mg, 0.684 mmol) and DIEA (177 mg, 1.37 mmol). The mixture was stirred at 60 C. overnight. Water (5 mL) was added to the mixture and the aqueous layer was extracted with EtOAc (2*10 mL). The combined organic layers were washed with water (2*10 mL) and brine, dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford (R)-methyl 2-(5-(ethoxycarbonyl)-4-(trifluoromethyl)pyrimidin-2-yl)-1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (75 mg, 57.8% yield) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,187035-79-6, Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Gregg, Richard E.; (82 pag.)US2016/113930; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 96833-41-9, 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 96833-41-9, name is 2-Chloro-4-methoxypyrimidin-5-amine. This compound has unique chemical properties. The synthetic route is as follows.

In a Shlenck reactor, a solution of 6-chloro-2-methoxy-3-nitropyridine (1.00 g, 5.30mmol), 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester (1.23 g, 5.83 mmol) andK3P04 (3.38 g, 15.90 mmol) in 1,4-dioxane (44 mL) and distilled water (9 mL) was degassed under N2. [1,1 ?-bis(diphenylphosphino)ferrocene] dichloropalladium (II), complex with dichloromethane (434.00 mg, 0.53 mmol) was added, the mixture was degassed again under N2 and heated at 80 C for 4 h. The mixture was extended withEtOAc and filtered on a pad of celite. The cake was washed with EtOAc and water. The layers were separated and the organic layer was dried over Mg504, filtered off and evaporated in vacuo to give a brown solid. The residue was purified by column chromatography on silica gel (irregular SiOH, 15-40 jim, 50 g, dry loading on celite, mobile phase: heptane/EtOAc, gradient: 95:5 to 60:40) to give 922 mg of intermediate138 (74% yield, yellow solid).

According to the analysis of related databases, 96833-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 302964-08-5 ,Some common heterocyclic compound, 302964-08-5, molecular formula is C16H13Cl2N5OS, 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.

Example 21; Procedure for the Preparation of Dasatinib Form L2A mixture of compound 1 (0.50 g, 1.27 mmol), N-(2-hydroxyethyl)piperazine (0.33 g, 2.54 mmol) and N-ethyldiisopropylamine (0.43 ml, 2.54 mmol) in DMSO (1.3 ml) was stirred at 80-85 C. for 2 hours. Butan-2-ol (7 ml) was slowly added at this temperature. The solution was slowly cooled to 0-5 C. The product was filtered off, washed with butan-2-ol (10 ml) and dried on the filter, than dried under reduced pressure at 40 C. for 6 hours. Yield: 0.56 g.

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. 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIMO, Ondrej; Filipcik, Jiri; Martaus, Alexandr; Jegorov, Alexandr; Gavenda, Ales; Aronhime, Judith; Vraspir, Pavel; Koltai, Tamas; Faustmann, Jiri; Gabriel, Roman; US2009/118297; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 38275-55-7, 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. 38275-55-7, name is 5-Fluoropyrimidine-2-carbonitrile, molecular formula is C5H2FN3, 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.

A round-bottom-flask containing 5-fluoropyrimidine-2-carbonitrile (Method 59, 1.50 g, 12.19 mmol) was charged with anhydrous THF (30 ml) under N2. The solution was cooled to 0 C, and a solution of MeMgBr (4.90 ml of a 3.0 M solution in ether, 14.62 mmol) was added dropwise. After 2 hours at 0 C, the reaction mixture was quenched with ice water and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, and evaporated to dryness to give the title compound as an oil (0.778 g, yield 46%). GC-MS, 140 (M); 1H NMR (CDCl3) delta 8.65 (s, 2H), 2.65 (s, 2H).

According to the analysis of related databases, 38275-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82392; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 1211443-58-1, name is 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C12H12ClN3O2

2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (1.07g, 4.03mmol), HBTU (1.53g, 4.03mmol) and diisopropylethylamine (2mL, 12.1mmol) are dissolves in dimethylformamide (20 mL). 2 M solution of dimethylamine in ethanol (2.4mL, 4.8 mmol) is added and the mixture is stirred for 30 minutes to achieve complete conversion. The reaction mixture is diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate, water, then brine. The organic phase is dried (Na2SC^), filtered and concentrated. Purification by chromatography on silicagel(ethyl acetate :heptane) provides 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6- carboxylic acid dimethylamide (927mg,79% yield) MS(ESI) m/z 293.1 (M+H)+

With the rapid development of chemical substances, we look forward to future research findings about 1211443-58-1.

Reference:
Patent; NOVARTIS AG; ASTEX THERAPEUTICS LTD.; BESONG, Gilbert; BRAIN, Christopher Thomas; BROOKS, Clinton A.; CONGREVE, Miles Stuart; DAGOSTIN, Claudio; HE, Guo; HOU, Ying; HOWARD, Steven; LI, Yue; LU, Yipin; MORTENSON, Paul; SMITH, Troy; SUNG, Moo; WOODHEAD, Steven; WRONA, Wojciech; WO2010/20675; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia