Day: March 5, 2021

Reference of 4316-97-6, 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 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of te/t-butyl-(3,4-cis)-3-fluoro-4-hydroxy-piperidine-1 -carboxylate (racemic) (1.0 g, 4.6 mmol) and 4,6-dichloro-5-methylpyrimidine (818 mg, 5.02 mmol) in anhydrous tetrahydrofuran (23 ml.) was added sodium hydride (201 mg, 5.02 mmol, 60% dispersion in mineral oil) in two portions at 0 degrees Celsius. After 18 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride and diluted with water. The resulting mixture was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a pale yellow oil (1.56 g, 99%). 1H NMR (400 MHz, deuterochloroform) delta 1.46 (s, 9 H), 1.84 – 1.91 (m, 1 H), 2.04 – 2.17 (m, 1 H), 2.24 (s, 3 H), 3.09 – 3.22 (m, 1 H), 3.29 – 3.43 (m, 1 H), 3.78 – 4.01 (m, 1 H), 4.09 – 4.20 (m, 1 H), 4.74 – 4.93 (m, 1 H), 5.31 – 5.43 (m, 1 H), 8.36 (s, 1 H). LCMS: (ES+): 346.4 (M+1 ).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 4316-97-6, 4,6-Dichloro-5-methylpyrimidine.

Reference:
Patent; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 22536-64-7, 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 22536-64-7, name is 2-Chloro-4-methoxy-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 8 4-Methoxy-6-methyl-2-(1,2,4-triazol-1-yl)-pyrimidine In anhydrous tetrahydrofuran, 159 mg of 2-chloro-4-methoxy-6-methylpyrimidine was substituted with 69 mg of 1,2,4-triazole. The reaction mixture was treated according to the procedure as in Example 5 to yield 92 mg of 4-methoxy-6-methyl-2-(1,2,4-triazol-1-yl)-pyrimidine, recrystallized from n-hexane, having a melting point of 142.5-143 C. NMR(CDCl3)delta: 2.53(1H,s), 4.07(1H,s), 6.57(1H,s), 8.13(1H,s), 9.20(1H,s).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 22536-64-7, 2-Chloro-4-methoxy-6-methylpyrimidine.

Reference:
Patent; Nissin Shokuhin Kabushiki Kaisha; US4849424; (1989); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 63558-65-6 ,Some common heterocyclic compound, 63558-65-6, molecular formula is C4H2ClIN2, 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 3: tert-Butyl (lR)-7-chloro-l-(5-formyl-2-methyi-3-thienyl)-3,4-dihydro-lH-isoquinoline- 2-carboxylate [00994] A solution of 4-chloro-5-iodopyrimidine (27.85 g, 1 16 mmol) in THF (280 mL) was cooled to -78 C with a dry-ice/MeOH bath. To the solution was added dropwise 2.50 M of n-BuLi in hexane (93 mL, 233 mmol) and the mixture was allowed to stir for 15 min at -78 C. To the mixture was added dropwise a solution of tert-butyl (lR)-7-chloro- l-(5-formyl-2-methyl-3- thienyl)-3,4-dihydro- lH-isoquinoline-2-carboxylate (27 g, 68.5 mmol) in THF (90 mL) at -75 C, and the resulting mixture was allowed to stir for 10 min at -40C followed by stirring for 30 min at 26 C. The reaction was quenched by addition of saturated aqueous NH4C1 (560 mL) and extracted with EtOAc (600 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo to provide 90 g of a maroon oil which was used without further purification. This step can also be done using a magnesium-halogen exchange (such as isopropylmagnesium chloride lithium chloride complex). Solvent for this transformation can alternatively comprise MeTHF. This reaction also can be run at 0 C to room temperature.The crude mixture was divided into three portions (30g, 59 mmol each) and each portion was dissolved in DCM (500 mL). Manganese (IV) oxide (86.7 g, 1 mol) was added to each solution and the reactions were allowed to stir at 30C for 4 h, at which point they were combined and filtered through a Celite pad. The filter cake was rinsed with DCM MeOH (100/1 , 500 mL x 3). The filtrate was concentrated in vacuo and the residue was purified by column chromatography eluting with 90/10 to 85/15 pentane/EtOAc gradient to provide 40 g (58% in 2 steps) of the title compound as a light yellow solid. The oxidation of tert-butyl ( l R)-7-chloro- l – (5-((4-chloropyrimidin-5-yl)(hydroxy)methyl)-2-methylthiophen-3-yl)-3,4-dihydroisoquinoline- 2(l H)-carboxylate can also be done using TEMPO/NaCIO reaction conditions. LCMS: (AA) M+Na 522.6.

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. 63558-65-6, 4-Chloro-5-iodopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DUFFEY, Matthew O.; ENGLAND, Dylan; FREEZE, Scott; HU, Zhigen; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; ONO, Koji; XU, He; (684 pag.)WO2016/4136; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 33034-67-2, 2-Chloro-4-(trifluoromethyl)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, HPLC of Formula: C5H2ClF3N2, blongs to pyrimidines compound. HPLC of Formula: C5H2ClF3N2

Step 7 To a solution of 1-isopropyl-7-(methylthio)-1,2,3,4-tetrahydropyrazino[1,2-a]indole (50 mg, 0.19 mmol) in iPrOH (2 mL) was added 2-chloro-4-(trifluoromethyl)pyrimidine (105 mg, 0.58 mmol) and DIEA (185 mg, 0.96 mmol). The mixture was stirred at 100¡ã C. for 4 h. The mixture was concentrated under vacuum and the residue was purified by preparative TLC to afford 1-isopropyl-7-(methylthio)-2-(4-(trifluoromethyl)pyrimidin-2-yl)-1,2,3,4-tetrahydropyrazino[1,2-a]indole (45 mg, 57.7percent yield) as a yellow oil. LC-MS MS (ESI) m/z 407.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33034-67-2, 2-Chloro-4-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Gregg, Richard E.; US2015/250787; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
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. 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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
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 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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia