Tag: M.W:100-200

Synthetic Route of 335654-06-3, 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.335654-06-3, name is 2-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

N-lodosuccinimide (742 g, 3.30 mol) was added to 2-chloro-7H-pyrrolo[2,3-c/]pyrimidine (482.5 g, 3.14 mol) in acetonitrile (2500 mL) at 12C. The mixture was stirred at room temperature for 1 hour then sodium metabisulphite (650 g in 4500 mL of water) was added. The mixture was stirred for 1 hour then filtered to afford the title compound as a orange solid in 82% yield, 716.2 g. 1H NMR (400 MHz, DMSO-d6): delta ppm 7.83 (s, 1 H), 8.63 (s, 1 H), 12.73 (s, 1 H)

The chemical industry reduces the impact on the environment during synthesis 335654-06-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER LIMITED; ANDREWS, Mark, David; BAGAL, Sharanjeet, Kaur; BROWN, David, Graham; GIBSON, Karl, Richard; OMOTO, Kiyoyuki; RYCKMANS, Thomas; SABNIS, Yogesh; SKERRATT, Sarah, Elizabeth; STUPPLE, Paul, Anthony; WO2014/53967; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1683-75-6, 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. 1683-75-6, name is 2-Amino-4-chloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below.

General procedure: To a mixture of (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-1H-benzo[d]imidazole derivatives (7 mmol, 1 eq.), which was commercially available or prepared according to the literature procedure [WO2016192630], amino aromatic chloride (1.1 eq.) in DMF (20 mL) was added Na2CO3 aq. (3 eq.). The mixture was bubbled with Ar for 15 mins and then Pd(dppf)Cl2 (0.1 eq.) was added. The mixture was heated to 80oC and stirred for 4-6 hours under Ar atmosphere, then cooled to room temperature and concentrated to remove the organic solvent after reaction completion. The residue was diluted with water (100 mL) and extracted with EA (150 mL×3). The organic layer was separated and washed with saturated brine, then dried with anhydrous Na2SO4. The organic phase was then concentrated and the residue was further purified with flash chromatography or preparative HPLC to afford the desired intermediate compounds 3a-3j, which were characterized by LC-MS.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1683-75-6, 2-Amino-4-chloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Zha, Chuantao; Deng, Wenjia; Fu, Yan; Tang, Shuai; Lan, Xiaojing; Ye, Yan; Su, Yi; Jiang, Lei; Chen, Yi; Huang, Ying; Ding, Jian; Geng, Meiyu; Huang, Min; Wan, Huixin; European Journal of Medicinal Chemistry; vol. 148; (2018); p. 140 – 153;,
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. 14160-93-1, name is 4-Amino-6-chloropyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below., Formula: C5H4ClN3O

Compound 1.2 (249 mg, 1.58 mmol, 1 eq.) and 2,4,6- trimethoxybenzylamine (free-based by saturated sodium bicarbonate wash) (313 mg, 1.59 mmol, 1 eq.) were dissolved in dichloromethane (3 mL) at room temperature. Acetic acid (91 muL, 1.58 mmol, 1 eq.) was added and the reaction mixture was heated in a microwave at 100C for 5 minutes. Sodium triacetoxyborohydride (410 mg, 1.94 mmol, 1.2 eq.) was added at room temperature and the reaction was stirred overnight. Saturated sodium bicarbonate solution and ethyl acetate were added to the reaction mixture and the layers were separated. The product was extracted twice more with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate solution, brine, and then dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the crude product was purified using silica gel column chromatography with a gradient of hexanes / ethyl acetate (l:l-M:2-»l:4-»0:100) followed by ethyl acetate / methanol (50:1) to afford compound 53.1 (287 mg, 0.846 mmol, 54%).

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, 14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde.

Reference:
Patent; SUNESIS PHARMACEUTICALS, INC.; WO2006/65703; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-66-9, 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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. A new synthetic method of this compound is introduced below.

To a solution of 0.07 g (0.19 mmol, 1.0 eq.) of(S)-1-amino-N-(3-chloro-4-fluorophenyl)-7- fluoro-2,3 -dihydro- 1H-indene-4-carboxami de hydrochloride (Vild) and 30 mg (0.21 mmol, 1.10 eq.) of 2-chloropyrimidine-4-carboxamide in 2 mL of NIVIP was added 0.07 ml (0.39mmol, 2.0 eq.) of N,N-diisopropylethylamine, and the mixture was subjected to microwave irradiation maintaining a reaction temperature of 130 C for 1 h. The mixture was diluted with 50 mL of ethyl acetate and washed 2 x 20 ml of water followed by 10 mL of brine. The organic phase was dried (Na2SO4), filtered and the solvent was removed in vacuo. The residue was purified by flash chromatography (Si02, eluting with a linear gradient of 0-30%ethyl acetate/hexanes) to provide 24 mg (0.05 mmol, 29%) of(S)-2-((4-((3-chloro-4- fluorophenyl)carbamoyl)-7-fluoro-2,3 -dihydro- 1H-inden- 1 -yl)amino)pyrimidine-4- carboxamide (104). LCMS: m/z found 444. 1/446.1 [M+H]. HPLC: RT = 4.13 mm (Method A); ?H NIVIR (300 MFIz, Methanol-d4) 8.50 (d, 1H), 7.93 (dd, 1H), 7.61-7.72 (m, 1H), 7.50- 7.60 (m, 1H), 7.16-7.28 (m, 2H), 7.03 (t, 1H), 5.88-5.95 (m, 1H), 3.07-3.48 (m, 2H), 2.55-2.66(m, 1H),2.10(m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-66-9, its application will become more common.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; COLE, Andrew, G.; DORSEY, Bruce, D.; KAKARLA, Ramesh; KULTGEN, Steven; QUINTERO, Jorge; (353 pag.)WO2018/172852; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 43212-41-5, 2,4-Dichloro-6-methoxypyrimidine, 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, 43212-41-5, blongs to pyrimidines compound. Recommanded Product: 43212-41-5

This product is mixed with morpholine in THF and stirred at 20-25 to give 6-methoxy-2-morpholino-4-chloropyrimidine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,43212-41-5, its application will become more common.

Reference:
Patent; Upjohn Company; US5099019; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 171178-33-9, 6-Chloropyrido[3,2-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, Application In Synthesis of 6-Chloropyrido[3,2-d]pyrimidin-4(3H)-one, blongs to pyrimidines compound. Application In Synthesis of 6-Chloropyrido[3,2-d]pyrimidin-4(3H)-one

Method A: To a solution of 6-chloro-pyrido[3,2-d]pyrimidin-4(3H)-one (200 mg,1.1 mmol) in 1 ,4-dioxane (20 ml) and water (10 ml) was added 3,4-dimethoxyphenyl boronic acid (240 mg, 1.32 mmol), potassium carbonate (380 mg, 2.75 mmol) and tetrakis(triphenylphosphine)palladium(0) (63 mg, 0.055 mmol). The reaction mixture was refluxed for 3 hours, cooled down to room temperature and the solvents were evaporated in vacuo. The residue was adsorbed on silica, purified by silica gel column chromatography (the mobile phase being a acetone/dichloromethane mixture, in a ratio gradually ranging from 30:70 to 40:60) and characterised by its mass spectrum as follows : MS (m/z) : 284 ([M+H]+, 100).Method B: A suspension of 2-carboxamido-3-amino-6-(3,4-dimethoxyphenyl)- pyridine (770 mg, 2.8 mmol) in triethyl orthoformate (28 ml) was refluxed for 12 hours. Then, the reaction mixture was cooled down and evaporated to dryness. The residue was purified by silica gel column chromatography (the mobile phase being an ethyl acetate/hexane mixture in a ratio gradually ranging from 2:8 to 3:7), resulting in the pure title compound (530 mg, yield 67 %) which was characterised by its mass spectrum as follows: MS (m/z) : 284 ([M+H)+, 100].

The synthetic route of 171178-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 4 AZA Bioscience nv; WO2006/135993; (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. 57473-32-2, name is 5,7-Dichloroimidazo[1,2-a]pyrimidine, molecular formula is C6H3Cl2N3, 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

Example 6: S-^SR^RJ-S-CCT-Chloroimidazotl^-fllpyrimidin-S-yO^ethylJamino)^- methylpiperidin-l-yl)-3-oxopropanenitrile (47)47To a stirred solution of 5,7-dichloroimidazo[l,2-a]pyrimidine (46) (0.082 g, 0.43 mmol) in dioxane (2 niL) was added 3-((3R,4R)-4-methyl-3-(methylamino)piperidin-l-yl)-3- oxopropanenitrile (21) (0.10 g, 0.43 mmol), sodium hydrogen carbonate (0.036 g, 0.43 mmol) and water (2mL). The mixture was subjected microwave irradiation (100 C, Power Max, Power 50w) for 30 minutes. The reaction mixture was concentrated in vacuum and the residue obtained was purified by flash chromatography (silica gel 12 g, eluting with CMA-80 in chloroform 0 to 100%). The product obtained was repurifed by flash chromatography [silica gel 12 g, eluting with a mixture of ethyl acetate and methanol (9:1) in hexanes (0 to 100%)] to afford 3-((3R,4R)-3-((7- Chloroimidazo [ 1 ,2-alpha]pyrimidin-5-yl)(methyl)amino)-4-methylpiperidin- 1 -yl)-3 -oxopropanenitrile (47) (14 mg, 9.38%) as a colorless solid. 1HNMR (300 MHz, DMSO, 380K) delta 7.68 (d, J= 1.6, IH), 7.61 (d, J= 1.6, IH), 6.65 (s, IH), 3.93 (d, J= 5.1, 2H), 3.88 – 3.79 (m, 2H), 3.65 (dd, J= 8.3, 13.7, IH), 3.46 (d, J= 35.6, 2H), 3.00 (s, 3H), 2.32 (d, J= 6.9, IH), 1.80 – 1.58 (m, 2H), 1.03 (d, J= 7.0, 3H); MS (ES+): 347.1 (M + 1), 369.0 (M+23).Compound 46 is commercially available from Toronto Research Chemicals, or it can be prepared as described by, Revankar, Ganapathi R. et al., Journal of Medicinal Chemistry, 1975, 7S(12); or G. R. Revankar and R. K. Robins, Ann. KY. Acad. ScL, 1975, 255, 166.

With the rapid development of chemical substances, we look forward to future research findings about 57473-32-2.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; CHAND, Pooran; KOTIAN, Pravin, L.; KUMAR, V., Satish; WO2010/14930; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3764-01-0 ,Some common heterocyclic compound, 3764-01-0, molecular formula is C4HCl3N2, 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 2-liter, 3-neck flask equipped with mechanical stirrer, thermometer and dropping funnel was loaded with ethanol (375 mL), water (375 mL) and morpholine, (1.01 mol, 88 g); the resulting solution was cooled (with sodium chloride- ice mixture) to about 0 0C and a solution of 2,4,6-trichloropyrimidine (91.17 g, 0.5 mol) in ethyl acetate (37.5 mL) was added dropwise in about 20 minutes, to maintain temperature below 10 0C. The dropping funnel was rinsed twice with ethyl acetate (3 mL), and the rinses were transferred to the reaction mixture. The reaction was checked by TLC to determine when the reaction was complete. After completion of the reaction, ice water (375 mL) was added, and reaction was allowed to stir for 30 minutes to complete precipitation. The colorless solid was filtered out, washed 6 times with water (225 mL per wash) and vacuum-dried at 40-50 0C until a constant weight of the product was maintained. The product (114.7 g, 98% yield) was a mixture of regioisomers 6-morpholino-2,4- dichloropyrimidine and 2-morpholino-4,6-dichloropyrimidine in about a 3.9:1 ratio which were separated by chromatograph to 6-morpholino-2,4-dichloropyrimidine.

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. 3764-01-0, 2,4,6-Trichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/124662; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5018-38-2, 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 5018-38-2 as follows.

4-(5-Methoxy-4-pyrimidinyl)-2-methylpiperazine Method 2 A solution of 2-methylpiperazine (20 g) in water (100 mL) was reacted with solid 4,6-dichloro-5-methoxypyrimidine (5.00 g, 27.9 mmole) in a procedure similar to that given for Method 2 of Example 14. After hydrogenation and filtration of the catalyst, the product was extracted from the filtrate with CH2 Cl2. The extracts were concentrated in vacuo, and the residue was Kugelrohr distilled to give a clear oil (5.46 g, 99.8%). The oil was dissolved in acetonitrile and concentrated HCl added to form the salt which was recrystallized from i-PrOH and dried in vacuo to give the product as a white powder (4.02 g, m.p. 185-188 C.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5018-38-2, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US5434154; (1995); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4316-93-2, 4,6-Dichloro-5-nitropyrimidine, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

To amino-acetic acid ethyl ester hydrochloride (1439.15 mg; 10.31 mmol; 1 .00 eq.) and 4,6-Dichloro-5-nitro-pyrimidine (2000.00 mg; 10.31 mmol; 1 .00 eq.) in dry DMF (26 mL) was added ethyl-diisopropyl-amine (3997.72 mg; 30.93 mmol; 3.00 eq.) and the mixture was stirred for 3 hours. LC-MS showed that the reaction was complete. The DMF was removed and the EtOAc was added.The mixture was washed with brine, dried over MgS04 and purified through flash chromatography on silica (EtOAc in Hexane from 0% to 30%) to provide (6-chloro-5-nitro-pyrimidin-4-ylamino)-acetic acid ethyl ester 2.1 g with 78% yield; LC/MS: 261 (M+H)

The synthetic route of 4316-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; LAN, Ruoxi; HUCK, Bayard R.; CHEN, Xiaoling; XIAO, Yufang; WO2014/78637; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia