Category: 63558-65-6

Application 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.

To a solution of lH-l,2,3-triazole (63.2 mg, 0.915 mmol) in THF (2.4mL), was added, portionwise, at 0C, NaH (39.9 mg, 0.998 mmol). After 30 minutes of stirring,4-chloro-5-iodopyrimidine (200 mg, 0.832 mmol) was added and the reaction mixture was allowed to come to room temperature, and stirred until judged complete by LCMS.To this was added aqueous saturated NH4C1, and the mixture was allowed to stir for 5 min at which time it was determined that the reaction was complete by LC-MS analysis.This reaction mixture was diluted with ethyl acetate and extracted twice. The combined organics were washed with brine and dried over Na2S04, filtered and concentrated in vacuo. The crude material was dissolved in a minimal amount of hexanes and loaded onto a silica gel column, the column was subsequently eluted as a gradient from 0-15%EtOAc/hexanes. The desired isomer was thus separated from the regioisomeric triazole adduct. The white solid attained (90mg, 39.6%) was determined to be the desired material by 1HNMR and LC/MS. MS (ES): m/z = 274.0 [M+H]+. ¾ NMR (400 MHz, CCI3D) delta ppm 9.34 (1 H, s), 9.15 (1 H, s), 8.03 (2 H, s).

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; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature 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.

To a solution of 4-amino-2,5-difluorophenol (0.190 g, 1.310 mmol) in DMF ( 10 mL) was added potassium ter/-butoxide (0.168 g, 1.497 mmol). The mixture was stirred at RT for 30 min. 4-Chloro-5-iodopyrimidine (0.30 g, 1.248 mmol) was added and the reaction mixture was heated at 80 C overnight. The reaction mixture was quenched with water and the solution was extracted with EtOAc (3x). The organic solution was washed with 5% aqueous lithium chloride solution and brine. The organics were dried over gS04, filtered, and concentrated. The crude was purified by silica gel column chromatography ( 10% to 50%EtOAc/hexane) to obtain 2,5-difluoro-4-(5-iodopyrimidin-4-yloxy)benzenamine (160 mg, 36.7%) yield) which was used for the next reaction. MS (ESI) m/z: 349.9 (M+H+).

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; DECIPHERA PHARMACEUTICALS, LLC; FLYNN, Daniel, L.; KAUFMAN, Michael, D.; WO2011/139891; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 63558-65-6, 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. 63558-65-6, name is 4-Chloro-5-iodopyrimidine, molecular formula is C4H2ClIN2, 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.

Step 7: (R) 4-[(lR)-7-Chloroisochroman-l-yl]-5-methyl-2 hienyl]-(4-chloropyrimidin-5- yl)methanol and (S)-[4-[(lR)-7-Chloroisochroman-l-yl]-5-methyl-2-thienyl]-(4-chloropyrimidin- 5-yl)methanol [00710] A solution of 4-chloro-5-iodopyrimidine (7.05 g, 29.3 mmol) in THF (100 mL) was cooled at -78 C. To the solution was added 2.50 M of n-BuLi in hexane (23.4 mL, 58.6 mmol) at the same temperature. After stirring for 10 min, a solution of 4-[(lR)-7-chloroisochroman- l -yl]-5-rnethyl- thiophene-2-carbaldehyde (7.15 g, 24.4 mmol) in THF (28.6 mL) was added at -78 C, and the resulting mixture was stirred for 10 min at the same temperature. The reaction was quenched by addition of water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (0 to 50% EtOAc in hexane) to give 9.34 g (94%) of the title compound mixture. NMR (400 MHz, DMSO-d6) delta 8.99 (s, 1 H), 8.94 (d, J = 3.1 Hz, 1 H), 7.23 (d, J = 2.6 Hz, 2H), 6.67 (d, J = 4.6 Hz, 1 H), 6.61 (d, J = 6.9 Hz, 1 H), 6.53 (d, J = 5.5 Hz, 1 H), 6.02 (dd, J = 8.1 , 4.6 Hz, 1 H), 5.74 (s, 1 H), 4.1 1 – 4.04 (m, 1 H), 3.84 – 3.74 (m, 1 H), 3.02 – 2.92 (m, 1 H), 2.73 (d, J = 16.6 Hz, 1 H), 2.37 (s, 2H), 2.36 (s, 1 H).

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 63558-65-6, 4-Chloro-5-iodopyrimidine.

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

Reference of 63558-65-6, 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 63558-65-6 as follows.

Step 2: torf-Butyl 3-[(4-chloropyrimidiii-5-yl)(b.ydroxy)methy]]-lH-pyrazole-l-carboxylate Into a flame dried RBF with stirbar was added 4-chloro-5-iodopyrimidine (12.3 g, 51 mmol) dissolved in THF (200 mL). The flask was purged with argon and cooled to -95 C. To this solution was added dropwise n-butyllithium (2.5 M in hexane; 43 mL, 107 mmol) at -95 C and the mixture was stirred for 10 min. To this mixture was added fert-butyl 3-formyl-lH-pyrazole-l-carboxylate (9.1 g, 46 mmol) dissolved in THF (30 mL) dropwise at -95 C. The reaction was stirred at -78 C for 30 min. The reaction was quenched with a solution of acetic acid (7.9 mL) in THF (15 mL) and then allowed to warm to rt. Water (80 mL) was added and the mixture extracted with EtOAc (3 ). The combined organic layers were then washed with water and brine, dried over Na2SC>4, filtered and concentrated. The crude product was purified on silica gel to give tert-butyl 3-[(4-chIoropyrimidin-5-yl)(hydroxy)methyl]-lH-pyrazole-l- carboxylate (10.2 g, 64%). LCMS (AA): m/z = 311 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63558-65-6, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 63558-65-6, 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. 63558-65-6, name is 4-Chloro-5-iodopyrimidine, molecular formula is C4H2ClIN2, 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.

Step 4: 6-Chloro-3′-[(5-iodopyrimidin-4-yl)amino]-N-[3-(trifluoromethyl)phenyl]biphenyl-3- carboxamideIn a screw-capped vial, 3′-amino-6-chloro-lambda^-[3-(trifluoromethyl)phenyl]biphenyl-3- carboxamide (240 mg TFA salt, 0.476 mmol) was mixed with 4-chloro-5-iodopyrimidine (0.131 g, 0.543 mmol) and isopropyl alcohol (2.0 mL), and the mixture was heated to 80 0C. After 16 h, the reaction was complete by LCMS (M+H 595/597, 3: 1). To the reaction mixture was added potassium carbonate solution. The resulting mixture was extracted with ethyl acetate and the organic extracts were washed with water, and then with saturated NaCl, and then dried (Na2SOzO and concentrated in vacuo to provide a residue (0.3g). TLC (30% EtOAc-hexane) Rf 0.19. The residue was purified by automatic flash chromatography on silica gel using a 12 g column; flow 30 mL/min; [A= hexane] [B= EtOAc ]. A, 4 min; Gradient to 30% B in 30 min. The product eluted in 26-32 min and the fractions were concentrated to give 0.19g of the purified product.

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 63558-65-6, 4-Chloro-5-iodopyrimidine.

Reference:
Patent; INCYTE CORPORATION; WO2008/79965; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 63558-65-6, 4-Chloro-5-iodopyrimidine, 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 63558-65-6, blongs to pyrimidines compound. Product Details of 63558-65-6

To a vial containing a solution of 4-chloro-5-iodopyrimidine (0.200 g, 0.832 mmol) in DMF (1.333 mL) was added morpholine (0.291 mL, 3.33 mmol) followed by cesium carbonate (0.542 g, 1.664 mmol). The vial was sealed with a Teflon cap and heated at 90C for 80 min, then allowed to cool to room temperature. The reaction mixture was filtered through a disposable fritted funnel and the filter cake washed with CH2CI2. The filtrate was concentrated, then further dried under high vacuum.Intermediate 105A: MS (ESI) : m/z = 292.0 [M+H]+ HPLC Peak ret. T = 1.23 minutes was product. (HPLC conditions: Column:Luna C18 4.6x30mm 3u A: 10:90 H20:ACN NH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow).

The synthetic route of 63558-65-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); 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. 63558-65-6, name is 4-Chloro-5-iodopyrimidine, molecular formula is C4H2ClIN2, 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. category: pyrimidines

To a stirred solution of 4-chloro-5-iodopyrimidine (300 mg, 1.248 mmol) in DMF (2 mL) was added cesium carbonate (813 mg, 2.496 mmol) and morpholine (0.435 mL, 4.99 mmol). The reaction was purged with N2, heated to 90 C for 12 hours and then concentrated to give the crude Intermediate 44, which was used directly in subsequent reaction. MS (ES): m/z = 292.1 [M+H]+. ‘H NMR (400 MHz, MeOD) delta ppm 8.69 (1 H, s), 8.56 (1 H, s), 3.76-3.86 (5 H, m), 3.61-3.71 (5 H, m). Intermediate 44 was used in the synthesis of Example 224.

With the rapid development of chemical substances, we look forward to future research findings about 63558-65-6.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; AUSTIN, Joel, Francis; SHARMA, Lisa, S.; BALOG, James, Aaron; HUANG, Audris; VELAPARTHI, Upender; DARNE, Chetan, Padmakar; SAULNIER, Mark, George; WO2012/15723; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 63558-65-6, 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. 63558-65-6, name is 4-Chloro-5-iodopyrimidine, molecular formula is C4H2ClIN2, 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.

EXAMPLE 5 Preparation of 4-chloro-5-phenylethynylpyrimidine A mixture of 2.1 g of 4-chloro-5-iodopyrimidine, 10 mL of triethylamine, 1.2 mL phenylacetylene, 80 mg copper iodide and 160 mg of dichlorobis(triphenylphosphine was stirred at room temperature for 18 hours. The mixture was diluted with dichloromethane and evaporated in vacuo. The residue was redissolved in a few mL of dichloromethane, 10 mL of triethylamine added and the mixture heated at reflux for one hour. The heterogeneous mixture was evaporated in vacuo and the residue obtained was partitioned between water and dichloromethane. A gelatinous precipitate which formed on shaking the two layers was filtered off, enabling separation of the two layers. The organic extracts were dried over sodium sulfate, filtrated and evaporated in vacuo to yield 2.5 g of a dark brown syrup. The syrup was purified by column chromatography on silica gel, twice, eluding with hexanes, 1:1 hexanes/dichloromethane, dichloromethane and finally ethyl acetate. Like fractions from dichloromethane elution were pooled, obtaining 350 mg of the product, 5-phenylethynyl-4-chloropyrimidine as an oil which solidified to white rosettes.

According to the analysis of related databases, 63558-65-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beauchamp, Lilia M.; Krenitsky, Thomas A.; Kelley, James L.; US2004/87789; (2004); 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 63558-65-6, name is 4-Chloro-5-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C4H2ClIN2

Step 1: (l-BenzyI-lH-pyrazol-3-yl)(4-chloropyrimidin-5-yl)methanol 4-Chloro-5-iodopyrimidine (300 mg, 1.25 mmol) was weighed into a 100 mL 2 necked RBF and the flask was purged with argon. This starting material was dissolved in THF (10 mL) and the solution was cooled to -78 C. To the solution was added n-Butyllithium (2.50 M in hexane; 1.0 mL, 2.5 mmol) at -78 C and then the mixture was stirred for 30 min. To this mixture was added dropwise a solution of 1 -benzyl- lH-pyrazole-3-carbaldehyde (211 mg, 1.1 mmol) in THF (4 mL), and the resulting mixture was stirred for 30 min. The reaction was quenched by addition of saturated NH4CI (50 mL) and extracted with EtOAc (50 mLx4). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified on silica gel to provide (1-benzyl- lH-pyrazol-3-yl)(4-chloropyrimidin-5-yl)methanol (304 mg, 85%) as a light yellow oil. LCMS (FA): m/z = 301.4 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 63558-65-6.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
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 63558-65-6, name is 4-Chloro-5-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C4H2ClIN2

Step 1: (l-BenzyI-lH-pyrazol-3-yl)(4-chloropyrimidin-5-yl)methanol 4-Chloro-5-iodopyrimidine (300 mg, 1.25 mmol) was weighed into a 100 mL 2 necked RBF and the flask was purged with argon. This starting material was dissolved in THF (10 mL) and the solution was cooled to -78 C. To the solution was added n-Butyllithium (2.50 M in hexane; 1.0 mL, 2.5 mmol) at -78 C and then the mixture was stirred for 30 min. To this mixture was added dropwise a solution of 1 -benzyl- lH-pyrazole-3-carbaldehyde (211 mg, 1.1 mmol) in THF (4 mL), and the resulting mixture was stirred for 30 min. The reaction was quenched by addition of saturated NH4CI (50 mL) and extracted with EtOAc (50 mLx4). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified on silica gel to provide (1-benzyl- lH-pyrazol-3-yl)(4-chloropyrimidin-5-yl)methanol (304 mg, 85%) as a light yellow oil. LCMS (FA): m/z = 301.4 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 63558-65-6.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia