Pyrimidines

Reference of 16097-63-5 ,Some common heterocyclic compound, 16097-63-5, molecular formula is C6H4ClF3N2S, 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 2-THIOMETHYL-4-CHLORO-6-TRIFLUOROMETHYLPYRIMIDINE] (1.9996 g, 8.75 mmol) in [MEOH] (50 mL) was added morpholine (1.5 mL, 17.2 [MMOL).] The solution was stirred overnight, concentrated in vacuo, and the resulting white solid was collected by vacuum filtration and washed with water. To a solution of the solid in [CH2C12] (50 mL) was added m- chloroperbenzoic acid (4.53 g, 26.3 mmol), and the resulting solution was stirred for 2 h at which time it was observed to be a white suspension. The solvent was removed in vacuo, and then [MEOH] (50 mL) was added followed by hydrazine monohydrate (3.0 mL, 61.8 mmol). The solution was stirred for 16 h, and was then concentrated to about one-half volume in vacuo. Water (100 mL) was then added to the resulting suspension, and the observed white solid was collected by vacuum filtration. This material was then washed with water and dried in vacuo to afford 1.7193 g of the title compound [(75%)] as a white solid. MH+ 264.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16097-63-5, its application will become more common.

Reference:
Patent; Smithkline Beecham corporation; WO2003/101442; (2003); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 1421372-94-2, 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. 1421372-94-2, name is N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine. A new synthetic method of this compound is introduced below.

Compound 6 (7.7 mL) was added to a suspension of N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine (compound 5, 15.5 g, 0.79) and K2CO3 (16.3 g) DMF (60 mL). The mixture was heated at 60 C. for 60 min and then water (150 mL) was added. Solids were filtered and rinsed with water. The crude dark red product was directly used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1421372-94-2, N-(4-Fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; X-Cutag Therapeutics, Inc.; CHENG, Changfu; WEN, Shuhao; LI, Hui Joyce; (30 pag.)US2019/169171; (2019); A1;,
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Pyrimidine – Wikipedia

Reference of 287714-35-6, 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.287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, molecular weight is 172.57, as common compound, the synthetic route is as follows.

Methyl 2-chloropyrimidine-5-carboxylate (0.927 g, 5.37 mmol) was added to a mixture of tert-butyl piperazine-l-carboxylate (1 g, 5.37 mmol) and DIPEA (2.34 mL, 13.4 mmol) in DCM (10 mL) in a 20 mL vial (exotherm). The reaction was then stirred at room temperature (bath temp). After 40 min, additional DCM (5 mL) was added along with an aqueous solution of 10 wt% citric acid (45 mL). The layers were separated, and the aqueous layer was extracted with DCM (10 mL). The combined organic layers were dried (Na2S04), concentrated under reduced pressure, and dried under high vacuum, giving 1.74 g (100%) of the title compound as a pale yellow-tan solid. LC/MS: m/z 323.0 (M+H)+, RT=1.00 min H NMR (400MHz, DICHLOROMETHANE-d2) delta = 8.82 (s, 2H), 3.89 (d, 7=4.5 Hz, 4H), 3.85 (s, 3H), 3.49 (t, 7=4.9 Hz, 4H), 1.47 (s, 9H)

Statistics shows that 287714-35-6 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloropyrimidine-5-carboxylate.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HARLING, John David; NEIPP, Christopher E.; PENDRAK, Israil; SMITH, Ian Edward David; TERRELL, Lamont Roscoe; YOUNGMAN, Mark; (120 pag.)WO2017/46036; (2017); A1;,
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Application of 274693-26-4, 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.274693-26-4, name is 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol, molecular formula is C26H32F2N6O4S, molecular weight is 562.63, as common compound, the synthetic route is as follows.

Charge (2.6 gm) of compound 28 in (8-10 Vol.) of Methanol at Room temperature. Charge dilute HC1 (1.4 gm) at RT. Stir the reaction mass for 24 hours at RT. Upon completion of the reaction checked by TLC, the reaction mass was brought to slightly acidic pH of 6-6.5 by using dilute aq. NaOH. Upon removal of methanol under vacuum and extracting organic mass with ethyl acetate and further washing this organic layer with brine and concentration of ethyl acetate under vacuum gave crude Ticagrelor 1. Further purification of Ticagrelor 1. was carried out by crystallization from a mixture of ethyl acetate and heptane to provide white to off-white solid. The purity of Ticagrelor 1 was 99.6% (HPLC). Some of the characteristic and selective peaks (delta value) in -NMR (CDG13) for 1 are 7.5 (s, 1H), 6.83 – 7.2 (m, 3H), 5.67 (m, 1 H), 5.04 (m, 1H), 4.82 (m, 1H), 4.13 (m, 1H), 3.6 – 3.9 (m, 4H), 3.2 (t, 2H), 1.57 (m, 2H), 0.79 (t, 3H).

Statistics shows that 274693-26-4 is playing an increasingly important role. we look forward to future research findings about 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol.

Reference:
Patent; ANLON CHEMICAL RESEARCH ORGANIZATION; RASADIA, Punitkumar Rameshbhai; RAMANI.Vaibhav Narendrakumar; PANDEY, Bipin; BHADANI, Vijay Nagjibhai; VACHHANI, Dipakkumar Dhanjibhai; SHAH, Anamik Kantilal; WO2015/162630; (2015); A1;,
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Pyrimidine – Wikipedia

Reference of 26452-81-3, 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. 26452-81-3, name is 4-Chloro-6-methoxypyrimidine, molecular formula is C5H5ClN2O, 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 microwave vial containing 4-chloro-6-methoxypyrimidine (0.290 g, 2.007mmol), (5-chloro-2-fluorophenyl)boronic acid (0.35 g, 2.007 mmol) and Na2CO3 (0.2 13 g, 2.007 mmol) in DME (10 mL), EtOH (1.250 mL) and water (1.250 mL) was purged with N2 for several mm. Then PdC12(dppf)-CH2C12 adduct (0.082 g, 0.100 mmol) was added and the vial was capped. The reaction was heated in a microwave at 100 °C for 1h. The reaction mixture was then diluted with water and extracted with EtOAc. Theorganic layer was washed with brine and then concentrated to give an orange-brownresidue. Purification by normal phase chromatography gave 4-(5 -chloro-2-fluorophenyl)- 6-methoxypyrimidine (400 mg, 84percent yield) as white crystals.4-Chloro-2-(6-methoxypyrimidin-4-yl)aniline was synthesized according to theprocedure described in Intermediate 5, by replacing (5-chloro-2-fluorophenyl)boronic acid with 4-chloro-2-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)aniline. MS(ESI) m/z:236.3 (M+H). ?H NMR (400MHz, CDC13) oe 8.78 (s, 1H), 7.49 (d, J=2.4 Hz, 1H), 7.15 (dd, J=8.6, 2.4 Hz, 1H), 6.99 (d, J0.9 Hz, 1H), 6.66 (d, J=8.6 Hz, 1H), 4.02 (s, 3H).

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 26452-81-3, 4-Chloro-6-methoxypyrimidine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3740-92-9, 4,6-Dichloro-2-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, Application In Synthesis of 4,6-Dichloro-2-phenylpyrimidine, blongs to pyrimidines compound. Application In Synthesis of 4,6-Dichloro-2-phenylpyrimidine

EXAMPLE 6 This Example illustrates the preparation of (E)-methyl 2-[2-(6-chloro-2-phenylpyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (Compound No.378 of Table II). A stirred solution containing (E)-methyl 2-(2-hydroxyphenyl)-3-methoxypropenoate (208mg) and 4,6-dichloro-2-phenylpyrimidine (225mg, prepared according to the method of D. B. Harden, M. J. Mokrose and L. Strekowski, J.Org.Chem, 1988, 53, 4137-4140) in DMF (5 ml) was cooled to 0° C. Potassium carbonate (138mg) was then added and stirring was continued at 0° C. under an atmosphere of nitrogen. After 3 hours, the temperature was allowed to rise to room temperature and stirring was continued overnight. The reaction mixture was diluted with water and then acidified with dilute hydrochloric acid. The resulting mixture was extracted with ether (*3) and the combined ether extracts were washed successively with dilute aqueous sodium hydroxide solution (*2) and water (*3) and then dried. Evaporation of the solvent gave an oil (0.31 g), which solidified on standing. Chromatography (eluent ether-hexane, 1:2) afforded the title compound (0.12 g, 30percent) as an off-white solid; m.p. 118-120° C.; 1H NMR: delta 3.54(3H,s), 3.67(3H,s), 6.65(1H,s), 7.22-7.50(7H,m), 7.44(1H,s), 8.28-8.33(2H,m) ppm; IR maxima: 1708, 1631 cm-1.

The synthetic route of 3740-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Clough, John Martin; Godfrey, Christopher Richard Ayles; Streeting, Ian Thomas; Cheetham, Rex; de Fraine, Paul John; Bartholomew, David; Eshelby, James John; US2003/60626; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 10070-92-5, 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. 10070-92-5, name is Pyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

EXAMPLE l N -[3-(cyclopentyloxy)phenyl]-2,2,2-trifluoro-N -(pyrimidin-5-ylmethyl)ethanesulfonamideDiisopropyl azodicarboxylate (0.45 mL, 2.3 mmol) was added dropwise to a stirred solution of 3-aminophenol (250 mg, 2.3 mmol), cyclopentanol (0.25 mL, 2.8 mmol), and triphenylphosphine (600 mg, 2.3 mmol) in tetrahydrofuran (1.4 mL) at 0 0C. After stirring for an additional 12hr at room temperature, the reaction mixture was rotovapped in vacuo to remove volatile solvents. The residue was directly purified via column chromatography on silica gel (eluting 5-50% EPO ethyl acetate/hexanes) to give 157 mg (40%) of [3-(cyclopentyloxy)phenyl]amine as red oil. To a solution of [3-(cyclopentyloxy)phenyl]-amine (157 mg, 0.89 mmol), pyrimidine aldehyde (96 mg, 0.89 mmol) and acetic acid (51 uL, 0.89 mmol) in dichloroethane 3.6 mL) was added sodium triacetoxyborohydride (283 mg, 1.3 mmol) at room temperature. The resulting mixture was stirred for an additional 2hr or until TLC indicated complete conversion. The reaction mixture was then rotovapped in vacuo to remove volatile solvents. The residue was directly purified via column chromatography on silica gel (eluting 15-100% ethyl acetate/hexanes) to give 200 mg (83%) of [3-(cyclopentyloxy)phenyl]- (pyrimidin-5-ylmethyl)amine as brown oil.A solution of 2,2,2-trifluoroethanesulfonyl chloride (0.1 ImL, l.Ommol) was added dropwise to a solution of [3-(cyclopentyloxy)phenyl](pyrimidin-5-ylmethyl)amine (200 mg, 0.74 mmol) in dichloroethane (2.8 mL) and pyridine (1.4 mL) at 00C. The reaction mixture was allowed to gradually warm to room temperature and then stirred at room temperature until TLC indicated completion of reaction. The solution was then rotovapped in vacuo to remove volatile solvents. The residue was directly purified via column chromatography on silica gel (eluting with 0-100% ethyl acetate/dichloromethane) to give N -[3-(cyclopentyloxy)phenyl]-2,2,2-trifluoro-N -(pyrimidin-5- ylmethyl)ethanesulfonamide as a solid. 1H NMR(CDCl3, 500MHz), delta 9.14 (s, IH), 8.61 (s, 2H), 7.29- 7.25 (m, IH), 6.87-6.85 (m, IH), 6.81-6.79 (m, IH), 6.72-6.71 (m, IH), 4.89 (s, 2H), 4.67-4.65 (m, IH), 3.88-3.83 (m, 2H), 1.90-1.61 (m, 8H). MS (ESI): 416 (M+ + H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10070-92-5, Pyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2006/49968; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 919116-36-2, 4-Chloro-2-(methylthio)-5-(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, Computed Properties of C6H4ClF3N2S, blongs to pyrimidines compound. Computed Properties of C6H4ClF3N2S

To a mixture of 4-(3-iodo-l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazolo[3,4-b]pyridin-6- yl)-3-methylisoxazole (952 mg, 2.32 mmol), 4-chloro-2-(methylthio)-5- (trifluoromethyl)pyrimidine (637 mg, 2.78 mmol), and hexamethylditin (486 uL, 2.32 mmol) in toluene (13 mL), purged with nitrogen (5 min), was added Pd(PPh3)4 (268 mg, 232 umol), and the reaction mixture was stirred at 105 C until full conversion (24 h). The reaction mixture was poured into a freshly prepared solution of aqueous potassium fluoride (1.0 g in 50 mL), and stirred for 30 min. The resulting mixture was filtered on Celite pad, and the filtrate was extracted with ethyl acetate (3×30 mL). The organic layers were combined, washed with brine (30 mL), dried over anh. Na2S04, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc in hexanes, 10 to 70% gradient) to afford the title compound (529 mg, 1.11 mmol, 48% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,919116-36-2, 4-Chloro-2-(methylthio)-5-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SYROS PHARMACEUTICALS, INC.; MARINEAU, Jason J.; CHUAQUI, Claudio; CIBLAT, Stephane; KABRO, Anzhelika; PIRAS, Henri; WHITMORE, Kenneth Matthew; LUND, Kate-Lyn; (200 pag.)WO2019/143719; (2019); A1;,
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Synthetic Route of 155-10-2, 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. 155-10-2, name is 4-Amino-2-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, 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 95 5-Fluoro-N2-[1-(2-phenyl-ethanesulfonyl)-piperidin-4-ylmethyl]-pyrimidine-2,4-diamine EXAMPLE 95 was prepared from C-[1-(2-phenyl-ethanesulfonyl)-piperidin-4-yl]-methylamine and 2-chloro-5-fluoro-pyrimidin-4-ylamine: MS (m+1)=394.5.

According to the analysis of related databases, 155-10-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Claiborne, Christopher F.; Butcher, John W.; Claremon, David A.; Libby, Brian E.; Liverton, Nigel J.; Munson, Peter M.; Nguyen, Kevin T.; Phillips, Brian; Thompson, Wayne; McCauley, John A.; US2002/165241; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 59950-53-7, name is 5-Aminopyrimidine-4-carboxylic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Aminopyrimidine-4-carboxylic acid

15 g of 5-aminopyrimidine-4-carboxylic acid was addedIn 200 ml of methanol,Add dropwise 10ml thionyl chloride, stirred at room temperature overnight, concentrated,Add 200 ml of toluene, concentrate,Get 18g 5-aminopyrimidine-4-carboxylate.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 59950-53-7, 5-Aminopyrimidine-4-carboxylic acid.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Bu Gonggaofamingren; (4 pag.)CN107176926; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia