Day: May 7, 2021

Synthetic Route of 149849-94-5, 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. 149849-94-5, name is Methyl 2-chloropyrimidine-4-carboxylate, molecular formula is C6H5ClN2O2, 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.

To a solution of methyl 2-chloropyrimindine-4-carboxylate (750 mg, 4.35 mmol) in methanol(20 mL) stirred under nitrogen at 0 C was added sodium borohydride (329 mg, 8.7 mmol)portion-wise. The reaction minxture was allowed to warm to rt and stirred at rt for 2 h. Asaturated solution of ammonium chloride in water (40 mL) and EtOAc (40 mL) were added.After separation, the aqueous layer was extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and evaporated in vacuo to afford a brown oil. This residue was purified by normal phase column chromatography [(EtOHIEtOAc 4: 1)/CyH 0-40%j to afford (2-chloropyrimindin-4-yl)methanol (187 mg, 1.3 mmol, purity: 42 %, recovery: 30 %) as a light yellow solid. LCMS (m/z) 145 and 147 (M+H), retention time: 1.26 min LC/MS Method 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 149849-94-5, Methyl 2-chloropyrimidine-4-carboxylate.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DAUGAN, Alain Claude-Marie; DONCHE, Frederic G.; FAUCHER, Nicolas Eric; GEORGE, Nicolas S.; (243 pag.)WO2018/92089; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 31462-59-6, 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.31462-59-6, name is Pyrimidine-4-carboxylic acid, molecular formula is C5H4N2O2, molecular weight is 124.1, as common compound, the synthetic route is as follows.

General Procedure 13 was followed in the preparation of Intermediate 19. 2129 General Procedure 13 2131 Intermediate 19 2132 [0243] Thionyl chloride (3.55mL, 48.4 mmol, 3 eq) was added dropwise to a solution of 2133 pyrimidine-4-carboxylic acid (2 g, 16.1 mmol) in EtOH (15 mL) and the resulting mixture 2134 was heated to reflux for 14 h. The mixture was then cooled to RT and made alkaline with 2135 saturated aqueous NaHC03 to pH 8. The basic solution was then extracted with EtOAc (4 x 2136 50 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04, 2137 filtered and concentrated in vacuo to afford Intermediate 19 (1.7g, 77%). 1H NMR: (DMSO- 2138 d6) 5 9.40 (d, J= 1.0 Hz, 1H), 9.10 (d, J= 5.1 Hz, 1H), 8.05 (dd, J= 5.1, 1.3 Hz, 1H), 4.39 2139 (q, J= 7.1 Hz, 2H), 1.35 (t, J= 7.1 Hz, 3H); MS: 153 [M + H]+; TLC: 40% hexane in EtOAc: 2140 Rf: 0.40

The chemical industry reduces the impact on the environment during synthesis 31462-59-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; VERSEON, INC.; SHORT, Kevin, Michael; PHAM, Son, Minh; WILLIAMS, David, Charles; KITA, David, Ben; WO2014/145986; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 941685-26-3, 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. 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

4- chloro-7 – ((2- (trimethylsilyl) ethoxy) methyl) -7H-pyrrolo [2,3-d] pyrimidine (Compound A, 500mg, 1.25mmol, 1.0eq) and5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane hetero-pentyl 2-yl) -7-tosyl–7H- pyrrolo [2,3-d] pyrimidine(Compound B, 392mg, 1.38mmol, 1.1eq) was dissolved in DME (10mL) mixture / 2M sodium carbonate solution (5mL) was added Pd (PPh3) 4 (144mg, 0.125mmol, 0.1eq) under N2 atmosphere, after addition was complete the reaction was warmed to reflux for 3h. TLC monitored the reaction was complete (Rf = 0.1, PE: EA = 3: 1), cooled to room temperature and added to H2O (30mL) and EA (50 mL) separated, aqueous phase extracted with EA three times, the combined organic phase was washed with saturated brine once, after the organic phase was dried over anhydrous magnesium sulfate, and column chromatography (PE: EA = 3: 1-1: 1) give 224 mg of a pale yellow solid (compound C).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Jiangsu Kefeiping Pharmaceutical Co., Ltd.; Nanjing Kefeipingshenghui Pharmaceutical Co., Ltd.; Nanjing Kefeiping Pharmaceutical Co., Ltd.; Qin Yinlin; Su Mei; Jin Qiu; Chen Tao; Wu Xianzhi; Jiang Jianhua; (15 pag.)CN105524067; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4595-59-9, 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 4595-59-9 as follows.

An oven dried 5 mL microwave vial with a 10 mm stir bar was charged with 5-bromopyrimidine (115 mg, 0.5 mmol), naphthalene-1-boronic acid (152 mg, 1.0 mmol) and tribasic potassium phosphate monohydrate (288 mg, 1.25 mmol). The vial was equipped with a septum and subjected to three evacuation/Argon backfill cycles. A toluene solution (0.1 mL) of Pd(OAc)2 (0.56 mg, 0.0025 mmol) and EvanPhos (1.8 mg, 0.0038 mmol) was added via syringe followed by toluene (0.9 mL). The reaction was stirred in an oil bath at 40 C. under argon. GC/MS monitoring showed complete consumption of the halide after 6 h. The vessel was cooled to rt and diluted with water (1 mL). The aqueous phase was extracted in flask with EtOAc (3*1 mL). The combined organic phases were flushed over a short plug of silica gel in a pasteur pipette and then washed with EtOAc. Volatiles were removed in vacuo. The mixture was chromatographed over silica gel eluting with 1:3 diethyl ether:hexanes (Rf=0.20, 3:7 diethyl ether:hexanes) which yielded an off-white powder (99 mg, 96%). 1H NMR (400 MHz, chloroform-d) delta 9.31 (s, 1H), 8.89 (s, 2H), 7.95 (dd, J=8.4, 3.7 Hz, 2H), 7.75 (d, J=8.2 Hz, 1H), 7.61-7.48 (m, 3H), 7.42 (d, J=7.0 Hz, 1H). 13C NMR (101 MHz, chloroform-d) delta 157.72, 157.40, 134.44, 133.87, 132.50, 131.26, 130.95, 129.53, 128.78, 127.84, 127.18, 126.54, 125.52, 124.65.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Reference:
Patent; The Regents of the University of California; Lipshutz, Bruce H.; Handa, Sachin; Landstrom, Evan; (35 pag.)US2018/117574; (2018); 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. 145783-15-9, name is 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine. A new synthetic method of this compound is introduced below., Safety of 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine

4,6-Dichloro-2-(propylthio)pyrimidin-5-amine (0.5 g, 2.1 mmol) was dissolved in methanol (2 mL) and supplemented with te/t-butylamine (460.0 mg, 6.3 mmol). The reaction mixture was introduced in a sealed vessel and heated at 100C for 24 h. After concentration of the reaction mixture to dryness under vacuum, the residue was purified by silica gel column chromatography. Yield: 88%. Melting point: 88-89C. *H NMR (DMSO -d6) d 0.95 (t, J=7.3 Hz, 3H, SCH2CH2C/ ,), 1.43 (s, 9H, NHC(C/ ,)3), 1.62 (h, J=7.3 Hz, 2H, SCH2CH2CH3), 2.95 (t, J=7.3 Hz, 2H, SCH2CH2CH3), 4.91 (bs, 2H, NH2), 6.19 (s, 1H, NHC(CH3)3). 13C NMR (DMSO -d6) d 13.3 (SCH2CH2CH3), 22.9 (SCH2CH2CH3), 28.5 (NHC(CH3)3), 31.9(SCH2CH2CH3), 51.9 (NHC(CH3)3), 120.3 (C-5), 137.6 (C-6), 152.1 (C-4), 154.5 (C-2).

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, 145783-15-9, 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine.

Reference:
Patent; UNIVERSITE DE LIEGE; LANCELLOTTI, Patrizio; OURY, Cecile; PIROTTE, Bernard; (140 pag.)WO2019/158655; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4270-27-3, 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. 4270-27-3, name is 6-Chloropyrimidine-2,4(1H,3H)-dione, molecular formula is C4H3ClN2O2, 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.

General procedure: 6-Chloropyrimidine-2,4(1H, 3H)-dione derivatives 1 (1.0 mmol) and N-hydroxyformimidoyl chloride derivatives 2 (1.2 mmol) were combined and dissolved in methanol (15mL), followed by the addition of triethylamine (3.0 mmol). Subsequently, the reaction mixture was stirred in a round-bottom flask (25mL) at room temperature for 5h. After completion of the reaction as indicated by TLC, the mixture was evaporated by rotary evaporator, extracted with ethyl acetate, dried over Na2SO4, then concentrated and purified by flash column chromatography (PE/EA=5:1) to yield compounds 3a-t.

According to the analysis of related databases, 4270-27-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Kun-Ming; Jin, Yi; Lin, Jun; Tetrahedron; vol. 73; 47; (2017); p. 6662 – 6668;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1032452-86-0, 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. 1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole, molecular formula is C13H10ClN3, 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.

4-Methylbenzenesulfonic acid hydrate (8.7 g) was added in one portion to 3-(2- chloropyrimidin-4-yl)-1-methylindole (9.3 g) and 4-fluoro-2-methoxy-5-nitroaniline (7.1 g) in nbutanol (200 mL). The resulting mixture was stirred at reflux for 1 h. The mixture was cooled to room temperature. The precipitate was collected by filtration, washed with n-butanol (50 mL), and dried under vacuum to afford N-(4-fluoro-2-methoxy-5-nitrophenyl)- 4-(1- methylindol-3- yl)pyrimidin-2-amine as a yellow solid (CompoundS, 15.5 g).

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 1032452-86-0, 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole.

Reference:
Patent; NEUFORM PHARMACEUTICALS, INC.; CHAORAN, Huang; CHANGFU, Cheng; (85 pag.)WO2017/117070; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1004-39-3, 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.1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol, molecular formula is C4H6N4S, molecular weight is 142.18, as common compound, the synthetic route is as follows.

General procedure: DBU (0.33 ml, 2.2 mmol) was added dropwise at roomtemperature to a stirred suspension of the respective thiol2a-n (2.2 mmol) in anhydrous MeCN (4 ml). The obtainedmixture was stirred for 15 min and then furoxan 1d (0.34 g,1.0 mmol) was added. The reaction mixture was furtherstirred for 48-120 h until complete conversion of thestarting furoxan 1d (control by TLC, eluent CHCl3). Thereaction mixture was then diluted with H2O (20 ml). The precipitate formed was filtered off, carefully washed withwater, 0.75 N NaOH, then again with water, acetonitrile(~1 ml), and air-dried.

The chemical industry reduces the impact on the environment during synthesis 1004-39-3, I believe this compound will play a more active role in future production and life.

Reference:
Article; Fershtat, Leonid L.; Epishina, Margarita A.; Kulikov, Alexander S.; Struchkova, Marina I.; Makhova, Nina N.; Chemistry of Heterocyclic Compounds; vol. 51; 2; (2015); p. 176 – 186; Khim. Geterotsikl. Soedin.; vol. 51; 2; (2015); p. 176 – 186,11;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 4595-59-9 , The common heterocyclic compound, 4595-59-9, name is 5-Bromopyrimidine, molecular formula is C4H3BrN2, 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 3 N-((1R,2R)-2-Hydroxy-cyclohexyl)-6-(2-pyrimidin-5-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinamidea) 5-Trimethylsilanylethynyl-pyrimidine; Tetrakis(triphenylphosphine)palladium(O) (727 mg, 0.6 mmol) was added to a stirred, degassed suspension of 5-bromopyrimidine (5.0 g, 31.4 mmol) and copper(I)iodide (120 mg, 0.6 mmol) in toluene and diisopropylamine (1:1, 200 ml) under nitrogen. The reaction mixture was heated to 60 C., trimethylsilylacetylene (4.89 ml, 34.6 mmol) was added and the reaction mixture was stirred for 3 hours at 60 C.. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate (200 ml) and washed with saturated aqueous ammonium chloride solution (3¡Á100 ml). The organic layer was separated, dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (5% ethyl acetate/heptane) to give 5-trimethylsilanylethynyl-pyrimidine as a pale brown solid, 4.71 g (85% yield). LC at 215 nm; Rt 2.07: 88%, m/z (ES+): 177 (M+H).

The synthetic route of 4595-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hebeisen, Paul; Roever, Stephan; US2008/70931; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10244-24-3, 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 10244-24-3 as follows.

Example 8: Preparation of Trianion of 5-bromo-4-(trifluoromethyl)pyridin-2-amine using 3.5 Equivalents of Isopropylmagnesium chloride, lithium chloride complexA reactor was charged with 5-bromo-4-(trifluoromethyl)pyridin-2-amine (1.000 g, 4.149 mmol) and tetrahydrofuran (7.72 ml). The mixture was sitrred for 10 minutes. The mixture was cooled to 0 C within 30 minutes. lsopropylmagnesiumcloride lithium chloride 1 .3M in THF (6.383 ml,8.298 mmol) was continuously added within a time period of 1.5 hours at 0 C. An additional1.5 equivalents of isopropylmagnesiumcloride lithium chloride 1 .3M in THF (4.788 ml, 6.224 mmol) was continuously added within a time period of 1 .5 hours at 0 C. An additional 0.5 equivalents of isopropylmagnesiumcloride lithium chloride 1 .3M in THF (1 .596 ml, 2.075 mmol) was continuously added within a time period of 1 hour at 0 C. The product was the trianion of 5-bromo-4-(trifluoromethyl)pyridin-2-amine, as determined by HPLC and LCMS.Example 9: Preparation of 5-(2,6-Di-4-morpholinyl-4-pyrimidin-4-yl)-4- (trifluoromethyl)pyridin-2-amine (Compound A)The compound 4,4?-(6-chloropyrimidine-2,4-diyl)dimorpholine (0.40g, 1.405 mmol), 1,1?- Bis(diphenylphosphino)ferrocene (0.040g, 0.070 mmol) and Palladium acetate (0.016g, 0.070 mmol) and 2 mL of tetrahydrofuran were placed in an inertized reactor. The reactor is evacuated to 100 mbar and flushed with nitrogen two times. lsopropylmagnesiumcloride lithium chloride 1 .3M in THF (1.405 mmol) was added at 30 C followed by an equivalent amount of the trianion of 5-bromo-4-(trifluoromethyl)pyridin-2-amine (1.405 mmol). The suspension was stirred for 0.5 hours. The product was 5-(2,6-Di-4-morpholinyl-4-pyrimidin-4-yl)-4- (trifluoromethyl)pyridin-2-amine, as determined by HPLC and LCMS.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10244-24-3, its application will become more common.

Reference:
Patent; NOVARTIS AG; FLUBACHER, Dietmar; BIERI, Nicole; ACEMOGLU, Murat; MICHEL, Pascal; MOSE, Rasmus; STETTLER, Hans; TESTA, Maria Caterina; BROZIO, Joerg; SCHAEFER, Frank; WO2014/64058; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia