Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 39551-54-7, 2,4-Dichloropyrido[3,2-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, 39551-54-7, blongs to pyrimidines compound. Quality Control of 2,4-Dichloropyrido[3,2-d]pyrimidine

To a solution of compound 88d (14.9 mg, 0.100 mmol) and 2,4-dichloropyrido[3,2-d]pyrimidine (11.6 mg, 0.158 mmol) in THF (2 mL) was added N,N-diisopropylethylamine (0.1 mL, 0.574 mmol). The mixture was stirred at rt for 1.5 h and at 50 C. for 30 min. The reaction mixture was then concentrated in vacuo, and the residue subjected to silica gel chromatography eluting with 20-70% EtOAc in hexanes to obtain compound 88e. LCMS-ESI+ (m/z): [M+H]+ calculated for C14H19ClFN4O: 313.12. found: 313.14; tR=1.06 min on LC/MS Method A.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39551-54-7, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Chin, Gregory; Mackman, Richard L.; Metobo, Samuel E.; Mish, Michael R.; Pyun, Hyung-jung; Zablocki, Jeff; (175 pag.)US2016/289229; (2016); A1;,
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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. 10070-92-5, name is Pyrimidine-5-carbaldehyde, molecular formula is C5H4N2O, 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. Computed Properties of C5H4N2O

To a 500 mL round bottom flask were added 150 g of a 3.4 wt% solution of 5- pyrimidinecarboxaldehyde in methanol (5.1 g, 0.047 mole contained 5-pyrimidine carboxaldehyde) and 20.9 g of a 28.2 wt% solution of sodium bisulfite in water (5.9 g, 0.057 mol contained sodium bisulfite). The resulting solution was then stirred for 30 min at ambient temperature. Most of the methanol was distilled off using a rotary evaporator at 50 C to give a light slurry, to which 40 mL of isopropyl alcohol was added. The resulting slurry was cooled down to ambient temperature and stirred overnight after which time the product was collected by filtration, washed with 15 mL of mixture of water and isopropyl alcohol (5 and 10 mL), and suction-dried at ambient temperature for 4 hours to give 16.6 g of white solid. Analysis of the product by NMR indicated 61 wt% of 5-pyrimidinecarboxaldehyde – sodium bisulfite adducts (quantitative yield from 5-pyrimidinecarboxaldehyde). ‘ H NMR (500 MHz, DMSO- d6) d 9.04 (s, 1H), 8.78 (s, 2H), 6.48 (b, 1H), 5.09 (d, J = 5.6 Hz, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 10070-92-5.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; DUMAS, Donald J.; HONG, Junbae; (65 pag.)WO2019/173173; (2019); A1;,
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Synthetic Route of 13544-44-0 ,Some common heterocyclic compound, 13544-44-0, molecular formula is C4HCl2IN2, 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.

(8.1.1 ) /V-te/f-butyl^-chloro-delta-iodopyrimidin^-amine. To a solution of 2,4-dichloro-5-iodopyrimidine (10 g, 36.4 mmol) in THF (150 ml.) and DIEA (5.17 g, 6.97 ml_, 40.0 mmol) was added dropwise a solution of tert-butylamine (2.85 g, 4.09 ml_, 38.9 mmol) in THF (15 ml_). The reaction was heated to reflux and stirred over weekend at reflux temperature. The reaction mixture was cooled to room temperature, diluted with EtOAc and washed with Na2CO3-solution (2x) and brine (1x). The organic layer was dried (Na2SO4) and concentrated in vacuo to give crude product, which was purified by column chromatography (SiO2, heptane/EtOAc; 100% heptane to 20% EtOAc as mobile phase) to give the title compound in 52% yield (5.84 g, 18.7 mmol).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13544-44-0, its application will become more common.

Reference:
Patent; N.V. ORGANON; PHARMACOPEIA, LLC; WO2009/124965; (2009); A1;,
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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 1146629-75-5, name is (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate. This compound has unique chemical properties. The synthetic route is as follows. Safety of (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate

6-(3-Nitrophenyl)-1H-indole (100 mg, 0.42 mmol) and (4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate (112 mg, 0.42 mmol) were dissolved in 1,4-dioxane (5 mL) in a sealed reactor and then Cs2CO3 (270 mg, 0.83 mmol) was added. After removing the gas included in the solution using ultrasonic wave and sequentially adding Xantphos (CAS No. 161265-03-8; 49 mg, 0.084 mmol) and Pd(OAc)2 (9.4 mg, 0.042 mmol), the reaction mixture was stirred at 120 C for 2 hours. After cooling to room temperature and adding ethyl acetate and water, the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, methylene chloride 100%) yielded (4-(6-(3-nitrophenyl)-1H-indol-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate (177 mg, 0.377 mmol) as white solid.MS m/z [M+1] 470.03; 1H NMR (400 MHz, DMSO-d 6) d 8.91 (s, 1H), 8.89 (s, 1H), 8.45 (s, 1H), 8.26 (d, J = 3.53 Hz, 1H), 8.20 (d, J = 8.23 Hz, 1H), 8.17 (d, J = 7.30 Hz, 1H), 7.85 (d, J = 7.65 Hz, 1H), 7.82 (d, J = 3.62 Hz, 1H), 7.78 (t, J = 7.97 Hz, 1H), 7.66 (dd, J = 5.8, 6.71 Hz, 1H), 7.03 (d, J = 3.79 Hz, 1H), 6.97 (d, J = 3.50 Hz, 1H), 6.30 (s, 2H), 1.10 (s, 9H).

With the rapid development of chemical substances, we look forward to future research findings about 1146629-75-5.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; SIM, Tae Bo; HAM, Young Jin; YOO, Kyung Ho; OH, Chang Hyun; HAH, Jung Mi; CHOI, Hwan Geun; KIM, Hwan; JUN, Eun Jin; WO2011/52923; (2011); A2;,
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Electric Literature of 161489-05-0, 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. 161489-05-0, name is 4-Iodo-6-methoxypyrimidine. A new synthetic method of this compound is introduced below.

To a solution of(S)-4-(difluoromethyl)-N-(6-(3,4-dimethylpiperazin-1- yl)-2,4-difluoro-3 -(1,2,3 ,6-tetrahydropyridin-4-yl)phenyl)-6-oxo- 1 ,6-dihydropyridine- 3-carboxamide (31.5 mg, 0.064 mmol, preparation described in Example 34) and 2- bromo-5-methoxypyrimidine (16.89 mg, 0.089 mmol) in 2-propanol (2.5 mL) at RT was added N,N-diisopropylethylamine (0.022 ml, 0.128 mmol). After heating in a microwave reactor at 170 C for 2 h, the reaction mixture was purified on preparatory column eluting with water (containing 0.1% HCOOH)/acetonitrile (containing 0.1% HCOOH) gradient (85/55). The title compound was isolated as an yellow powder (20 mg, 50%). LCMS [M+1j 602.5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,161489-05-0, its application will become more common.

Reference:
Patent; PROPELLON THERAPEUTICS INC.; AL-AWAR, Rima; ISAAC, Methvin; JOSEPH, Babu; LIU, Yong; MAMAI, Ahmed; PODA, Gennady; SUBRAMANIAN, Pandiaraju; UEHLING, David; WILSON, Brian; ZEPEDA-VELAZQUEZ, Carlos Armando; (311 pag.)WO2019/46944; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 60025-09-4, 4-Amino-6-chloropyrimidine-5-carbonitrile, 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, Computed Properties of C5H3ClN4, blongs to pyrimidines compound. Computed Properties of C5H3ClN4

e) (S)-4-Amino-6-(2-(5-(methylsulfonyl)-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yI)pyrrolidin-1 -yI)pyrimidine-5-carbonitrileA solution of (S)-5-(methylsu lfonyl)-3-phenyl-2-(pyrrolid in-2-yl)quinazolin-4(3H)-one (38 mg,0.10 mmol) and 4-amino-6-chloropyrimidine-5-carbonitrile (CAS registry 60025-09-4) (15.9mg, 0.10 mmol) in EtCH (1 ml) was treated with DIPEA (0.045 ml, 0.26 mmol) and wasstirred at 120C for 45 mm in mw. The reaction mixture was evaporated under reducedpressure. The oil was taken up in DCM and washed with sat. aq. NHCO3soln., the organic layer was dried over Na2SO4 and concentrated in vacuo. The crude was purified over SFC (column PPU, 250 x30 mm, 60A, 5pm, Princeton, flow at 100 mI/mm; gradient of MeCH in supercritical CC2, from 18 % to 23 % in ii mm) to afford the title compound as a beige solid(33 mg, 63 % yield).HPLC RtM2=0.87 mm; ESIMS: 488 [(M+H)].1H NMR (400 MHz, DMSC-d6): O 8.24 (dd, 1 H), 7.85-8.05 (m, 3 H), 7.50-7.70 (m, 5 H),7.24 (br s, 2 H), 4.50 – 4.75 (m, 1 H), 3.99 – 4.16 (m, 1 H), 3.80 – 3.97 (m, 1 H), 3.48 (5, 3 H),2.18 -2.31 (m, 1 H), 2.05 -2.18 (m, 1 H), 1.78- 2.03 (m, 2 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60025-09-4, 4-Amino-6-chloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; GUIBOURDENCHE, Christel; HINTERMANN, Samuel; HURTH, Konstanze; JACQUIER, Sebastien; KALIS, Christoph; MOEBITZ, Henrik; SOLDERMANN, Nicolas; WO2014/128612; (2014); A1;,
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Synthetic Route of 633328-98-0, 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.633328-98-0, name is 5-Chloro-1H-pyrazolo[4,3-d]pyrimidine, molecular formula is C5H3ClN4, molecular weight is 154.5571, as common compound, the synthetic route is as follows.

Step 1A mixture of of 5 -chioro- 1 H-pyrazolo [4,3 -d]pyrimidine (1 g, 6.47 mmol) and NIS (1.747 g, 7.76 mmol) in acetonitrile (6 mL) in a microwave sealed tube was heated to 120C for 40 mm in an oil bath. Then the reaction was cooled down and concentrated to dryness. The residue was purified via gradient C18 chromatography [ISCO, 0 – 100 % water(0.1% TFA) in acetonitrile(0,1% TFA)] which furnished Intermediate Hi.

Statistics shows that 633328-98-0 is playing an increasingly important role. we look forward to future research findings about 5-Chloro-1H-pyrazolo[4,3-d]pyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEMONG, Duane; GRESHOCK, Thomas, J.; CHANG, Ronald, K.; DAI, Xing; LIU, Hong; MCCAULEY, John, A.; LI, Wei; BASU, Kallol; SCOTT, Jack, D.; MILLER, Michael; WO2015/26683; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine, 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, name: 2-Methanesulfonyl-4,6-dimethoxypyrimidine, blongs to pyrimidines compound. name: 2-Methanesulfonyl-4,6-dimethoxypyrimidine

EXAMPLE 1 Preparation of 5-(4,6-dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene (Compound No. 104) A mixture comprising 2.1 g of 4-formyl-5-hydroxy-3-methylbenzothiophene, 2.4 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.8 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 70 C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 3.1 g (yield: 86%) of the desired compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US5616537; (1997); A;,
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. 1514-96-1, name is 4-Chloro-2-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, 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 1514-96-1

To a stirred solution of tert-butyl 4-[(2-{[6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 Hbenzimidazol-2-yl]amino}pyridmn-4-yl)methyl]piperazine-1 -carboxylate (500 mg, 936 pmol) and4-chloro-2-(trifluoromethyl)pyrimidine (307 mg, 1.68 mmol) in dioxane (5 mL) and water (0.9 mL) was added sodium carbonate (297 mg, 2.81 mmol) and Pd(dppf)C12 . CHCl (115 mg, 140 pmol). The mixture was heated to reflux for 24 h. Dichioromethane was added, the mixture was dried (magnesium sulfate), filtered and the solvent was removed in vacuum. Silicagel chromatography gave 540 mg (83 % yield) of the title compound.LC-MS (Method 2): Rt = 1.40 mm; MS (ESIpos): m/z = 555 [Mi-H]

With the rapid development of chemical substances, we look forward to future research findings about 1514-96-1.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
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Electric Literature of 22536-65-8, Adding some certain compound to certain chemical reactions, such as: 22536-65-8, name is 2-Chloro-5-methoxypyrimidine,molecular formula is C5H5ClN2O, 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 22536-65-8.

[0595] Synthesis of methyl 5-methoxypyrimidine-2-carboxylate: [0596] To a stirred solution of 2-chloro-5-methoxypyrimidine (1 g, 6.92 mmol) in MeOH: CH3CN (4: 1, 20 mL) under argon atmosphere were added Pd(dppf)Cl2 (1 g, 1.38 mmol) and triethyl amine (1.9 mL, 13.84 mmol) at RT; heated to 100 C and stirred for 16 h in steel bomb under CO pressure. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 60% EtOAc/ Hexanes to afford methyl 5-methoxypyrimidine-2-carboxylate (600 mg, 52%) as brown solid. [0597] 1H-NMR (CDC13, 400 MHz): delta 8.54 (s, 2H), 4.06 (s, 3H), 4.00 (s, 3H); LC-MS: 98.52%; 169 (M++l); (column: X Bridge C-18, 50 3.0 mm, 3.5 mupiiota); RT 2.26 min. 0.05% Aq TFA: ACN; 0.8 mL/min); TLC: 70% EtOAc/ Hexanes (R 0.2).

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. 22536-65-8, 2-Chloro-5-methoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
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