Day: May 10, 2021

Related Products of 15783-48-9, 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 15783-48-9, name is 2,4-Dichlorofuro[3,4-d]pyrimidin-7(5H)-one. This compound has unique chemical properties. The synthetic route is as follows.

2,6-Dihydroxypyrimidine-4-carboxylic acid (100 g, 73.4 mmol) and paraformaldehyde (84 g, 293 mmol) were combined with concentrated HCl (1.5L) and heated to reflux at 85-95 C for 18 hours. The reaction was then cooled and HCl was evaporated under reduced pressure to obtain a solid. The solid was washed with petrolium ether to give crude 2,4-dihydroxyfuro[3,4- d]pyrimidin-7(5H)-one (90 g, 83 % yield) which was used next tep without further purification.[0113] A mixture of 2,4-dihydroxyfuro[3,4-d]pyrimidin-7(5H)-one (lOOg, 595mmol), phosphoryl trichloride (800mL) and N,N-diethylaniline (150 mL) was heated at 110 C for 18 hours. The reaction was cooled to ambient temperature, the solvent was removed in vacuo to give a residue. The residue was purified on a silica gel column eluted with petroliumether_EtOAc=5: l to give 2,4-dichlorofuro[3,4-d]pyrimidin-7(5H)-one (70 g, 57 % yield) as an off-white solid.[0114] A solution of 2,4-dichlorofuro[3,4-d]pyrimidin-7(5H)-one (34g, 165mmol) in DCM (770 mL) was added 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (24 g, 165 mmol) was cooled to 0 C and then triethylamine (96 mL, 660mmol) was added dropwise. The mixture was then concentrated in vacuo to give a residue which was purified on a silica gel column eluted with DCM_EtOAc=l :2 to give 4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chlorofuro[3,4-d]pyrimidin- 7(5H)-one (28 g, 82% yield) as a yellow solid. MS [M+H] found 282.[0115] Under a nitrogen at 0 titanium chloride triisopropoxide (1 M in hexanes) (75 ml, 75 mmol) was added to a solution of 4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chlorofuro[3,4- d]pyrimidin-7(5H)-one (19 g, 68 mmol) in THF (100 mL) followed by dropwise addition of ethylmagnesium bromide (1 M in THF) (150 ml, 150 mmol). The reaction was warmed up to ambient temperature and stirred overnight and then quenched by addition of a saturated NH4C1 solution (200 mL). The water layer was extracted with ethyl acetate, and the combined organic layers were dried over Na2S04, filtered, and evaporated in vacuo to give a residue. The residue was purified on a silica gel column eluted with petrolium ether_EtOAc=3: l to give l-(6-(8-oxa- 3-azabicyclo[3.2.1 ]octan-3-yl)-2-chloro-5-(hydroxymethyl)pyrimidin-4-yl)cyclopropanol (5 g, 24% yield) as a yellow solid. MS [M+H] found 312.[0116] To a solution of l-(6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-5- (hydroxymethyl)pyrimidin-4-yl)cyclopropanol (3 g, 9.6 mmol) and PPh3(2.5 g,14.4 mmol) in dry THF (200 mL) was added DEAD (3.77 g,14.4 mmol) dropwise at 0 C. The mixture was stirred at ambient temperature for 3 hours. The solvent was removed in vacuum to give a residue which was purified on silica gel column eluted with petroleum ether_EtOAc=4: l to give a residue which was further purified by Prep HPLC (Column: Fuji CI 8 (300×25); Wavelength 220 nm; Mobile phase: A MeCN (0.1% TFA); B water (0.1% TFA); Flow rate: 25 mL /min; Injection volume: 2 mL; Run time: 20 min; Equilibration: 3 min) to give 4′-(8-oxa-3- azabicyclo[3.2.1 ]octan-3-yl)-2′-chloro-5’H-spiro[cyclopropane- 1 ,7′-furo[3,4-d]pyrimidine] (330mg, 12% yield). MS [M+H] found 294.[0117] A mixture of 4′-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2′-chloro-5’H-spiro[cyclopropane- l,7*-furo[3,4-d]pyrimidine] (10.2 mg, 0.035 mmol), l-Methyl-3-[4-(4,4,5,5-Tetramethyl-l,3,2- dioxaborolane-2-yl)phenyl]-urea (19.18 mg, 0.069 mmol), sat. NaHC03 aq. (0.25 ml, 0.035 mmol) and PdCl2(dppf)-CH2Cl2 (2.269 mg, 2.78 muiotaetaomicron) in 1 ,4-Dioxane (0.5 ml) was heated by microwave at 110 C for 30 min. The mixture was passed throught filter and washed with MeOH. The filtrate was purified by preparative HPLC (gradient 20-45% ACN (containing 0.035% TFA) in water (containing 0.05% TFA). The fractions containing the desired compound were combined and concentrated in vacuo to give a solid. This solid was partitioned between EtOAc and NaHC03 aq. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaCl, dried and concentrated in vacuo to give a beige solid, which was triturated with hexane/ethyl acetate (1 : 1), collected by filtration, rinsed with hexane/ethyl acetate (1 :1) and dried to give the title compound (10.1 mg, 0.025 mmol, 71.4 % yield) as a beige solid. 1H NMR (400 MHz, DMSO- 6) delta ppm 1.09 (m, 2 H) 1.18 (m, 2 H) 1.78 (m, 4 H) 2.65 (s, 3 H) 3.25 (m, 2 H) 3.95 (m, 2 H) 4.43 (m, 2 H) 5.32 (s, 2 H) 6.12 (br s, 1 H) 7.47 (d, J=8 Hz, 2 H) 8.14 (d, J= 8 Hz, 2 H) 8.81 (s, 1 H). MS [M+H] found 408.

According to the analysis of related databases, 15783-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; JIN, Bohan; LARDY, Matthew; ZHOU, Feng; DONG, Qing; WO2012/99581; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5305-40-8, 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.5305-40-8, name is 4,6-Dichloropyrimidine-5-carbaldehyde, molecular formula is C5H2Cl2N2O, molecular weight is 176.9882, as common compound, the synthetic route is as follows.

Preparation of 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine: 4,6-Dichloro-pyrimidine-5-carbaldehyde hydrazine (10 mL, excess), and dioxane (90 mL) are combined at -78 C. in THF. The reaction solution is warmed to rt and stirred for 16 hr. The solvent is evaporated in vacuo to provide a crude residue which is diluted with dichloromethane (600 mL). The organic solution is washed with water (50 mL), brine (50 mL) and dried over anhydrous sodium sulfate. The solvent is removed in vacuo to provide 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine as a yellow powder which is used without further purification.

The chemical industry reduces the impact on the environment during synthesis 5305-40-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ChemoCentryx, Inc.; US2007/10523; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 39906-04-2 ,Some common heterocyclic compound, 39906-04-2, molecular formula is C5H5Cl2N3, 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 mixture of 4,6-dichloro-2-methylpyrimidin-5amine(1 g, 5.62 mmol) and O-ethyl carbonisothiocyanatidate(0.66 ml., 5.62 mmol) was added toluene (2 mL) to wet thesolids completely. The mixture was placed on 1000 C. oil bathfor 1.5 hours, at which time, the mixture had seized to give asolid mass. The solids were cooled to ambient temperatureand triturated with ether, then the resulting solids were collectedby filtration to give ethyl 7-chloro-5-methylthiazolo[5,4-d]pyrimidin-2-ylcarbamate (1.08 g, 3.96 mmol, 70.5%yield).

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. 39906-04-2, 4,6-Dichloro-2-methylpyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, JAMES H; MCDONALD, IVAR M; KING, DALTON; OLSON, RICHARD E; WANG, NENGHUI; IWUAGWU, CHRISTIANA I; ZUSI, F.CHRISTOPHER; MACOR, JOHN E; (330 pag.)JP5714745; (2015); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1004-39-3 ,Some common heterocyclic compound, 1004-39-3, molecular formula is C4H6N4S, 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.

EB1 Schiff base was synthesized by reaction of 30mL of ethanol hot solution (60 C) of bisaldehyde (2,2?-(ethane-1,2-diylbis(oxy))dibenzaldehyde) (1 g, 3.7¡Á10-3mole) and 30 mL hot ethanol solution (60 C) of (hydrazine carbothioamide) (0.674 g, 7.4¡Á10-3mole) in ratio (1:2). In preparation of L1 Schiff base 30 mL of ethanol hot solution (60 C) of bisaldehyde (2,2?-(ethane-1,2-diylbis(oxy))dibenzaldehyde) (1 g, 3.7¡Á10-3mole) was mixed with 30 mL hot ethanol solution (60 C) (4,6-diaminopyrimidine-2-thiol) (0.525 g, 3.6¡Á10-3mole) in ratio (1:1). Then sulfuric acid was added to eliminate water through condensation, and then the reaction mixture was left under reflux for 2 h. The formed solid Schiff?s bases were separated by filtration and purified by crystallization from ethanol. This preparation can be summarized in the following Scheme 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1004-39-3, its application will become more common.

Reference:
Article; Zayed, Ehab M.; Zayed; El-Desawy; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 134; (2015); p. 155 – 164;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 31058-83-0 , The common heterocyclic compound, 31058-83-0, name is 6-Chloro-N,N-dimethylpyrimidin-4-amine, molecular formula is C6H8ClN3, 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.

A mixture ofN-(cis-4-bromo-2-trifluoromethoxy-benzyl)-cyclohexane-1, 4- diamine (466 mg), (6-chloro-pyrimidin-4-yl) -dimethyl-amine (200 mg), and ethylene glycol (0.5 mL) was stirred at reflux for 4 hr in a sealed tube. The mixture was poured into saturated aqueous NaHC03 and the aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromatography (NH-silica gel, 50% EtOAc in hexane and silica gel, 501-‘o MeOH in CHCl3) to give N’- (cis-4- { [4-bromo-2- (trifluoromethoxy) benzyl] amino} cyclohexyl)-N, N-dimethylpyrimidine-4, 6-diamine. To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure. The residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to give N’-(cis-4-{[4-bromo-2- (trifluoromethoxy) benzyl] amino} cyclohexyl)-N,N-dimethylpyrimidine-4, 6-diamine dihydrochloride (67 mg). ESI MS m/e 488, M (free) + H+ ;’H NMR (300 MHz, CDC13) 8 1.64-1. 86 (m, 2 H), 1.96- 2.34 (m, 8 H), 2. 98-3.44 (m, 8 H), 4.27 (s, 2 H), 7.40-7. 59 (m, 3 H), 8.06-8. 24 (m, 2 H).

The synthetic route of 31058-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2434-53-9, name is 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione

Mixture of 6-amino-1-methyl-pyrimidine -2,4 (1H, 3H) – dione(5.46g, 40.0mmol) and bromo succinimide (7.56g, 42.0mmol) in acetonitrile (100 mL) solution was heated to reflux under nitrogen protection for 1.5 hours. The reaction was cooled to room temperature, filtered, (20 mL) and washed to remove the solvent, the resulting solid was washed with water, and dried to give 6-amino-5-bromo-1-methyl-pyrimidine -2,4 (1H, 3H)-dione (8.6g, white solid), yield: 98%

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, 2434-53-9, 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Sichuan Gooddoctor Pharmaceutical Group Co., Ltd.; Wu, Lingyun; Zhang, Peng; Zhang, Li; Li, Jian; Chen, Shuhui; Geng, Funeng; Chen, Yongmei; Liu, Bin; Ma, Xiuying; (109 pag.)CN105566324; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 22536-63-6, name is 2-Chloro-4-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Chloro-4-methoxypyrimidine

Reference Example 24 N-(4-Iodophenyl)-4-methoxy-N-methylpyrimidin-2-amine [Show Image] (1) Under an argon atmosphere, sodium hydride (100 mg) was added to a solution of 4-iodoaniline (220 mg) and 2-chloro-4-methoxypyrimidine (145 mg) in anhydrous DMF (10 ml), and the resulting mixture was stirred at 125C for 21 hours. The reaction solution was cooled to room temperature and water was added thereto, followed by extracting the resulting mixture with ethyl acetate. Organic layer was washed twice with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate = 10/1) to obtain N-(4-iodophenyl)-4-methoxypyrimidin-2-amine (46 mg).

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, 22536-63-6, 2-Chloro-4-methoxypyrimidine.

Reference:
Patent; Toray Industries, Inc.; EP2042171; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1749-68-4, 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.1749-68-4, name is 6-Chloro-2-methylpyrimidin-4-amine, molecular formula is C5H6ClN3, molecular weight is 143.57, as common compound, the synthetic route is as follows.

The 6-amino-4-(1-indolinyl)-2-methylpyrimidine was obtained as a solid, m.p. 209-210 C., in a similar number to that described for the analogous intermediate in Example 51 by reaction of 6-amino-4-chloro-2-methylpyrimidine with indoline.

The chemical industry reduces the impact on the environment during synthesis 1749-68-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Imperial Chemical Industries Plc; US5223505; (1993); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 54326-16-8, 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. 54326-16-8, name is 5-Chloropyrimidin-2(1H)-one, molecular formula is C4H3ClN2O, 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.

I. N-(5-tert-butyl-isoxazol-3-yl)-N’-{4-[6-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea hydrochloride [Compound B12] was also prepared by first preparing the benzothiazole starting material, 5 methoxy-benzothiazol-2-yl-amine: To prepare the 5-methoxy-benzothiazol-2-ylamine starting material: To a suspension of (3-methoxy-phenyl)-thiourea (1.822 g, 10 mmol) in CH2Cl2 (20 mL) at 0 C. was added dropwise a solution of bromine (1.76 g, 11 mmol) in 10 ml of trichloromethane over a period of thirty minutes. The reaction was stirred for 3 hours at room temperature then heated to 3 hours to reflux for one hour. The precipitate was filtered and washed with dichloromethane. The solid was suspended in saturated NaHCO3 and extracted with CH2Cl2. The extract was dried over MgSO4 and concentrated to give a white solid (1.716 g, 95%). To prepare the 2-amino-benzothiazol-5-ol: To a suspension of 5-methoxy-benzothiazol-2-ylamine in 16 mL of 48% HBr/H2O was heated to 105 C. in an oil bath for 10 hours. After the reaction was cooled to room temperature, the precipitate was collected by filtration and washed with acetone. The filtrate was suspended in saturated NaHCO3 and extracted with CH2Cl2. The extract was dried over MgSO4 and concentrated to give a white solid (0.986 g, 63%). N-(5-tert-butyl-isoxazol-3-yl)-N’-{4-[6-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea hydrochloride 2-amino-benzothiazol-5-ol from the previous step and following the method described in 1H NMR (DMSO-d6) ? 11.1 (br, 1H), 9.69 (br, 1H), 9.28 (br, 1H), 8.71 (s, 1H), 7.97 (d, 1H), 7.79 (d and s, 3H), 7.56 (d, 2H), 7.13 (dd, 1H), 6.53 (s, 1H), 4.56 (t, 2H), 3.98 (m, 2H), 3.82 (t, 2H), 3.65 (m, 2H), 3.55 (m, 2H), 3.25 (m, 2H), 1.31 (s, 9H); LC-MS: ESI 561 (M+H)+. [Compound B12]

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 54326-16-8, 5-Chloropyrimidin-2(1H)-one.

Reference:
Patent; Bhagwat, Shripad; Chao, Qi; Grotzfeld, Robert M.; Patel, Hitesh K.; Sprankle, Kelly G.; US2007/232604; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 108831-66-9, 6-Methyl-3H-thieno[2,3-d]pyrimidin-4-one, 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: C7H6N2OS, blongs to pyrimidines compound. HPLC of Formula: C7H6N2OS

General procedure: A mixture of thienopyrimidinone (0.01 mol), POCl3 (11 mL) and PCl5 (1.5 g) was quickly heated to 105 C and boiled for 5-6 h. The solvent was evaporated. Dry product was dissolved in methylene chloride (12 mL) and neutralized by cold solution of NaOH (0.5 N). The organic phase was separated and dried over Na2SO4, filtered, and then solvent was evaporated in vacuum. The residue was crystallized from isopropyl alcohol. Yield 80%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,108831-66-9, 6-Methyl-3H-thieno[2,3-d]pyrimidin-4-one, and friends who are interested can also refer to it.

Reference:
Article; Ostrynska, Olga V.; Balanda, Anatoliy O.; Bdzhola, Volodymyr G.; Golub, Andriy G.; Kotey, Igor M.; Kukharenko, Olexander P.; Gryshchenko, Andrii A.; Briukhovetska, Nadiia V.; Yarmoluk, Sergiy M.; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 148 – 160;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia