Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-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, 130049-82-0, blongs to pyrimidines compound. Application In Synthesis of 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one

Example 1 – Synthesis of 3-[2-[4-(6-fluoro-1,2-benzoisoxazol-3-yl)-1-piperidinyl]ethyl-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one hydrochloride (Paliperidone hydrochloride) 6-Fluoro-3-(4-piperidinyl)-1,2-benzoisoxazole hydrochloride (300 g, 1.17 mols), 3-(chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (343 g, 1.40 mols) and triethylamine (272 g, 2.69 mols) are suspended in methanol (1.5 1) in a 3000 ml reactor under nitrogen atmosphere, and the reaction mixture is heated at reflux temperature for 18-20 h. Conversion to the product is checked by HPLC titre, obtaining a yield of 96.5% in solution. The mixture is concentrated to a residue. The so obtained product has an XRPD spectrum as shown in Figure 5, and a DSC thermogram as shown in Figure 6, which are characteristic of paliperidone crystalline Form I. The mixture is taken up with demineralised water (1.5 1) and 36.5% hydrochloric acid (113 g, 1.13 mols), obtaining a solution with a pH of 3-4. A solid then reprecipitates, and the mixture is cooled to 0C and filtered. The solid is washed with demineralised water cooled to 0-5C (2 x 150 ml), and then with acetone cooled to 0-5C (3 x 200 ml). The solid is dried in oven under reduced pressure at a temperature of 50C for 16-18h. 451 g of paliperidone hydrochloride is obtained, with a potentiometric titre of 99.9%, an argentimetric titre of 7.8%, 99.2% HPLC purity, and a total yield of 90%. The product has an XRPD spectrum as shown in Figure 1, and a DSC thermogram as shown in Figure 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,130049-82-0, its application will become more common.

Reference:
Patent; Dipharma Francis S.r.l.; EP2243780; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 153435-63-3 ,Some common heterocyclic compound, 153435-63-3, molecular formula is C16H30N2Sn, 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.

i) A solution of 3-(tributylstannyl)pyridine (0.449 g, 1.22 mmcl) and methyl 5-bromofuran-2-carboxylate (0.250 g, 1.22 mmol) in DMF (13 mL) was degassed with Ar. CsF (0.556 g, 3.66 mmol), CuCI (0.016 g,0.159 mmcl) and tetrakis(triphenylphosphine)palladium (0.071 g, 0.061 mmol) were added and the RM was heated at 110 C by microwave irradiation for 1 h. The RM was diluted with water (50 mL) and extracted with EtOAc (2x 50 mL). The combined organic layer was washed with brine (2x 50 mL), dried over Na2SO4 and concentrated in vacuo. FC (EtOAc/heptane 1:19 -> 4:6) afforded INT-IOA (0.215 g, 1 .06 mmol, 87%) as a pale yellow solid. LCMS: calc. for [M-f-H]=204.06, found 204.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; NARDI, Antonio; RATCLIFFE, Paul; CRAAN, Tobias; HERTRAMPF, Thorsten; LESCH, Bernhard; KIME, Robert; STEINHAGEN, Henning; WO2015/161928; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 93366-88-2, 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.93366-88-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-2-amine, molecular formula is C6H6N4, molecular weight is 134.14, as common compound, the synthetic route is as follows.

7H-pyrrolo[2,3-d]pyrimidin-2-amine (134 mg, 1.00 mmol), 2-bromo-5-fluoro-4-iodopyridine (604 mg, 2.00mmol),potassium carbonate (415 mg, 3.00 mmol) and proline (23 mg, 0.2 mmol) was added to the eggplant flask,dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (19 mg, 0.1 mmol) was added and the reaction solution was deoxygenated. Heat to 90 C and stir for 16 hours. After the reactionwas completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over celite. The target compound was obtained in 246 mg.

Statistics shows that 93366-88-2 is playing an increasingly important role. we look forward to future research findings about 7H-Pyrrolo[2,3-d]pyrimidin-2-amine.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 63200-54-4, 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.63200-54-4, name is 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H3Cl2N3, molecular weight is 188.0141, as common compound, the synthetic route is as follows.

2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (134 mg, 0.71 mmol), NaHCO3 (66 mg, 0.78 mmol) and Pd/C (1.52 mg, 10%) were mixed in EtOH (4 ml). Hydrogen (3 psi) was applied and the mixture was stirred for 2.5 hours at room temperature. The mixture was passed through a plug of celite and the filtrate was evaporated. The residue was purified by flash chromatography to afford 90 mg (88%) of the title compound. LC/MS (20-100% CH3CN:0.05% HCOOH(aq) gradient over 5 min): 1.58 min. 154 M+H.

The chemical industry reduces the impact on the environment during synthesis 63200-54-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; Schnute, Mark Edward; Wennerstal, Goeran Mattias; Blinn, James Robert; Kaila, Neelu; Kiefer, JR., James Richard; Mente, Scot Richard; Kurumbail, Ravi G.; Meyers, Marvin Jay; Thorarensen, Atli; Xing, Li; Zapf, Christoph Wolfgang; Zamaratski, Edouard; Flick, Andrew Christopher; Jones, Peter; (77 pag.)US2016/46597; (2016); 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 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 582313-57-3

To a solution of trans-4-(dimethylamino)cyclohexan-l-ol (280 mg, 1.95 mmol, 3.90 equiv) in tetrahydrofuran (5 mL) was added sodium hydride (200 mg, 5.00 mmol, 9.97 equiv, 60percent). The mixture was stirred at 0°C for 30 min. Then 4-chloro-5-fluoro-7H-pyrrolo[2,3- d]pyrimidine (86 mg, 0.50 mmol, 1.00 equiv) was added. The resulting solution was stirred for 16 h at 70°C. The resulting solution was extracted with 5×15 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product (70 mg) was purified by Prep-HPLC with the following conditions: Column, SunFire Prep CI 8, 19* 150mm 5um; mobile phase, Water with 50mmol NH4HCO3 and CH3CN (5.0percent CH3CN up to 25.0percent in 10 min, up to 95.0percent in 2 min,down to 5.0percent in 2 min); Detector, uv 254/220nm. This resulted in 31 mg (22percent) of trans-4-([5-fluoro-7H-pyrrolo[2,3- d]pyrimidin-4-yl]oxy)-N,N-dimethylcyclohexan-l -amine as a off-white solid. LC-MS: (ES,m/z): 279 [M+H] + 1H NMR (300 MHz, CD3OD, ppm): delta 1.64-1.38 (m, 4H), 1.99-2.07 (m, 2H), 2.25- 2.40 (m, 9H), 5.16-5.20 (m, 1H), 6.96 (d, 1H), 8.25 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 582313-57-3.

Reference:
Patent; NIMBUS IRIS, INC.; HARRIMAN, Geraldine C.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; WESSEL, Matthew David; GREENWOOD, Jeremy Robert; WO2014/11911; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 7033-39-8, 5-Bromo-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, 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, Formula: C6H7BrN2O2, blongs to pyrimidines compound. Formula: C6H7BrN2O2

Example 79; 5-(8-{ [(2,6-Dimethylphenyl)methyl] amino}-2,3-dimethylimidazo [1 ,2-a] pyridin-6- yl)-l,3-dimethyl-2,4(lNo.,3H)-pyrimidiiiedione hydrochlorideA mixture of iV-[(2,6-dimethylphenyl)methyl]-2,3-dimethyl-6-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)imidazo[l,2-alpha]pyridin-8-amine ( ~1.4 mmol; crude product from Description 45) and 5-bromo-l,3-dimethyluracil (310 mg, 1.4 mmol) in 2M aqueous sodium carbonate (1.5 mL) and dimethylformamide (3 mL) was degassed with argon and then treated with [1,1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium (10 mg, 0.01 mmol). The mixture was heated in an Initiator Microwave Synthesizer at 100C for 2 hours. The resulting reaction mixture was applied to an Isolute SCX cartridge. Elution with methanol, then 2M NH3 in methanol gave, after evaporation, the crude product which was purified by silica gel chromatography eluting with ethyl acetate/hexane EPO mixtures. The product was dissolved in methanol (5 mL) and then IM HCl in diethyl ether (0.5 mL) was added. After stirring for 10 minutes, the solvents were evaporated to yield the title compound. MS (ES+ve): [M+H]+ at m/z 418 (C24H27N5O2 requires [MHhH]+ at m/z 418).

The synthetic route of 7033-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/100119; (2006); 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. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine, molecular formula is C5H5ClN2S, 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. Quality Control of 4-Chloro-2-(methylthio)pyrimidine

General procedure: alpha,beta-unsaturated tosylhydrazones 1 (0.11 mmol, 1.1 equiv), heteroaryl chlorides 2 (0.1 mmol, 1 equiv), Cs2CO3 (0.25 mmol, 2.5 equiv) and MeCN (1 mL) were added to a tube. The mixture was stirred at 60 C until the heteroaryl chlorides was completely disappeared for 4-8h. After cooling to room temperature, the mixture was quenched with NH4Cl (2 mL, saturated aqueous solution) and extracted with CH2Cl2 (3 × 2 mL). The combined organic phases were dried over Na2SO4 and solvents removed in vacuo. The residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:10-1:4, V/V) as the eluent, affording the desired product 3 and 4.

With the rapid development of chemical substances, we look forward to future research findings about 49844-90-8.

Reference:
Article; Zeng, Lin; Guo, Xiao-Qiang; Yang, Zai-Jun; Gan, Ya; Chen, Lian-Mei; Kang, Tai-Ran; Tetrahedron Letters; vol. 60; 33; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5305-59-9, 6-Chloropyrimidin-4-amine, 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, 5305-59-9, blongs to pyrimidines compound. category: pyrimidines

Add in the reaction flask4-amino-6-chloropyrimidine (6 g, 46.5 mmol),Tetrahydrofuran (75 mL) and pyridine (9.0 mL).Cyclopropylcarbonyl chloride (5.3 g, 50.7 mmol) was added dropwise at room temperature.10 minutes after the drop finished,The reaction solution was heated to 60 C,The reaction was incubated for 3 hours.After the reaction solution was cooled,Diluted with water (100 mL)Ethyl acetate was extracted twice,The organic phase was combined and used1N hydrochloric acid and saturated brine and dried.After concentration,Heated with n-hexane,To give N- (6-chloropyrimidin-4-yl)Cyclopropylcarboxamide(Pale yellow solid, 4.2 g, 45.8%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5305-59-9, its application will become more common.

Reference:
Patent; Zhang, Ruihao; (36 pag.)CN105949178; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 62458-96-2, 7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-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, Computed Properties of C14H15N3O, blongs to pyrimidines compound. Computed Properties of C14H15N3O

A 2-necked 1 liter KBF (round bottom flask) was charged with ethyl l-benzyl-3- oxopiperidine-4-carboxylate (30 g, 101 mmol), formamidine acetic acid salt (10.5 g, 101 mmol) and EtOH (450 mL). The resulting mixture was stirred at 0C and treated with NaOEt (21% in EtOH) (112.6 mL, 299 mmol). The reaction mixture was heated at 60 C overnight and monitored for completion via LCMS and TLC (DCM:MeOH::95:5) (DCM – dichloromethane). Additional starting carboxylate (1 g) was added, followed by another gram of the same after 12 h with continued heating at 60 C. The reaction was complete after 4 h as indicated by LCMS. The cooled reaction was concentrated under vacuum and the residue was treated with cone. HCl (300 mL) and stirred overnight at room temperature. The solvents EPO were removed under vacuum and the resulting solids were treated with EtOH (300 mL), stirred for 15 minutes and then filtered to furnish 44g of crude 7-benzyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one as the HCl salt, which was used as such for the next step without further purification.LCMS (0.1% formic acid modifier) calculated. (M+l)+ 242.12, observed 242.3.1H NMR (CD3OD) (free base) delta 7.98 (s, 1 H), 7.35 – 7.32 (m, 5 H), 3.72 (s, 2 H), 3.41 – 3.40 (m, 2H),2.75 (t, J= 5.7 Hz, 2 H), 2.57 (m, 2 H).

The synthetic route of 62458-96-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WO2007/28022; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 7627-39-6, name is 2,4-Dichloro-5-(ethoxymethyl)pyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 7627-39-6

Sodium bicarbonate (700.67 mg, 8.34 mmol) was added to 4 mL of dry DMSO.2,4-dichloro-5 -(ethoxymethyl)pyrimidine (172.7 mg, 0.8300 mmol) was added followed by glutathione (256.32 mg, 0.83 00 mmol). The reaction was stirred at room temperature for 48 h. Once judged complete, the reaction was filtered and then diluted with 0.5 mL of water and purified directly by reverse phase prep-HPLC (10-95% MeCN/Water, 0.1% TFA) to give (2S)-2- amino-5 -oxo-5 – [[( 1R)-2-(carboxymethylamino)- 1 -[ [2-chloro-5 -(ethoxymethyl)pyrimidin-4- yl]sulfanylmethyl]-2-oxo-ethyl]amino]pentanoic acid (25 mg, 0.0523 mmol, 6.3 % yield) (VI-) MS m/z (M+H)= 478.14.

The synthetic route of 7627-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE CAR LLC; GUO, Jian; MALONA, John; RUCHELMAN, Alexander L.; SURAPANENI, Sekhar S.; (158 pag.)WO2018/170200; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia