Pyrimidines

Synthetic Route of 2164-66-1, 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. 2164-66-1, name is Methyl 2-aminopyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

2-Amino-4-methoxycarbonylpyrimidine (3.0g, 20mmol, Reference Compound No.3-1) was suspended in a mixture solvent of ethanol (150mL) and dichloromethane (20mL), then sodium borohydride (2.2g, 59mmol) was added thereto at room temperature, and the whole was stirred for 24 hours. Acetone (20mL) was added gradually under ice-cooling, and then 2M hydrochloric acid was added until the bubbles were no longer formed. Saturated aqueous sodium hydrogencarbonate solution was added to adjust the pH of the reaction mixture to 8, and the precipitated solid was filtered out. The filtrate was concentrated under reduced pressure, then suspended in a 10percent methanol-chloroform solution, and the mixture was filtered again with silica gel (5.0g). The filtrate was evaporated under reduced pressure, the precipitated solid was filterd off with ethyl acetate, and dried under reduced pressure to give 1.8g of the title Reference Compound as a pale yellow solid (Yield: 73percent) 1H-NMR (400MHz, DMSO-d6) delta 4.30(s,2H),5.35(s,1H),6.48(s,2H),6.65(d,J = 4.9 Hz,1H),8.19(d,J = 4.9 Hz,1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2164-66-1, its application will become more common.

Reference:
Patent; SANTEN PHARMACEUTICAL CO., LTD.; EP1864977; (2007); A1;,
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Pyrimidine – Wikipedia

Reference of 84905-80-6, 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.84905-80-6, name is 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

To a solution of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (1.0 g), 1-bromo-2-chloroethane (930 mg) in N,N-dimethylformamide (25 mL) was added potassium carbonate (1.5 g), and the mixture was stirred at room temperature for 2 hr. Saturated brine was added to the reaction system under ice-cooling, and the mixture was extracted twice with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=1:0?1:1) to give the title compound (806 mg) as yellow crystals. 1H-NMR (DMSO-d6) delta: 3.97-4.06 (2H, m), 4.65-4.76 (2H, m), 6.51 (1H, d, J = 3.0 Hz), 7.72 (1H, d, J = 3.0 Hz), 8.74 (1H, s)

Statistics shows that 84905-80-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2103620; (2009); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 39551-54-7, 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. 39551-54-7, name is 2,4-Dichloropyrido[3,2-d]pyrimidine, molecular formula is C7H3Cl2N3, 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.

2,4,-dichloropyrido[3,2-d]pyrimidine (80 mg, 0.39 mmol, 1 equiv.) was treated with THF (10 ml) followed by N,N-diisopropylethylamine (0.28 mL, 1.5 mmol, 4 equiv.), and then (R)-methyl 2-amino-5,5-difluorohexanoate 79C (110 mg, 0.39 mmol, 1 equiv., TFA salt). The reaction mixture was stirred for 1 h to form 79D and then this solution was used directly. LCMS (m/z): 345.11 [M+H]+; tR=1.09 min. on LC/MS Method A.

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 39551-54-7, 2,4-Dichloropyrido[3,2-d]pyrimidine.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Chin, Gregory; Mackman, Richard L.; Metobo, Samuel E.; Mish, Michael R.; Pyun, Hyung-jung; Zablocki, Jeff; (175 pag.)US2016/289229; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 7226-23-5 ,Some common heterocyclic compound, 7226-23-5, molecular formula is C6H12N2O, 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 28 3-Cyclopentyl-N-pyridin-2-yl-2-(4-pyridin-3-yl-phenyl)-propionamide A solution of diisopropylamine (17.1 mL, 122.21 mmol) in dry tetrahydrofuran (55 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (18 mL) was cooled to -78 C. under nitrogen and then treated with a 10M solution of n-butyllithium in hexanes (12.2 mL, 122.21 mmol). The yellow reaction mixture was stirred at -78 C. for 30 min and then treated dropwise with a solution of 4-iodophenylacetic acid (15.25 g, 58.19 mmol) in dry tetrahydrofuran (55 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (18 mL). The reaction mixture turned dark in color and was allowed to stir at -78 C. for 45 min, at which time, a solution of iodomethylcyclopentane (13.45 g, 64.02 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was allowed to warm to 25 C. where it was stirred for 42 h. The reaction mixture was concentrated in vacuo to remove tetrahydrofuran and then quenched with a 10% aqueous hydrochloric acid solution (100 mL). The resulting aqueous layer was extracted with ethyl acetate (3*200 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1*200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid (13.97 g, 70%) as a cream solid: mp 121-122 C.; EI-HRMS m/e calcd for C14H17IO2 (M+) 344.0273, found 344.0275.

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. 7226-23-5, 1,3-Dimethyltetrahydropyrimidin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Corbett, Wendy L.; Haynes, Nancy-Ellen; Sarabu, Ramakanth; US2002/2190; (2002); 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. 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, 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. Formula: C6H5ClN4

General procedure: A mixture of chloro compound (50 mg) and amine derivative (2 equiv.) in PEG 400 (2 mL) wasstirred at 120 C for 5 min. After completion the reaction was then cooled to room temperature. DCM and water were added and the phases were separated. The aqueous phase was extracted withDCM and the organic phase was dried and filtered. The removal of solvent gave the product as solid.

With the rapid development of chemical substances, we look forward to future research findings about 24415-66-5.

Reference:
Article; Campos, Joana F.; Loubidi, Mohammed; Scherrmann, Marie-Christine; Berteina-Raboin, Sabine; Molecules; vol. 23; 3; (2018);,
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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. 1004-40-6, name is 6-Amino-4-hydroxy-2-mercaptopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Amino-4-hydroxy-2-mercaptopyrimidine

General procedure: To 1.9 g (20 mmol) of pyrrolidin-2-one in 5 mL of 1,4-dioxane at 0-5C while vigorously stirring was added dropwise 2.74 g (20 mmol) of PCl3. The reactionmixture was stirred for 15 min at 30 and during 10min was gradually added 10 mmol of compounds 4-6 or 10-12 dissolved in minimal amount of 1,4-dioxane. The reaction mixture was stirred for 3 h at 60C, the temperature was raised to 100C and the stirring continued for 15 min more. After cooling 50 mL of ice cold water was added, the solution was filtered from a little amount of precipitate, the filtrate was neutralized with 30% NH4OH and held for one day at 5C. The formed precipitate was filtered off and dried in air.

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, 1004-40-6, 6-Amino-4-hydroxy-2-mercaptopyrimidine.

Reference:
Article; Gasparyan; Alexanyan; Arutyunyan; Kocharov; Martirosyan; Tamazyan; Ayvazyan; Panosyan; Danagulyan; Russian Journal of Organic Chemistry; vol. 52; 11; (2016); p. 1646 – 1653; Zh. Org. Khim.; vol. 52; 11; (2016); p. 1652 – 1658,7;,
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Application of 89581-38-4 ,Some common heterocyclic compound, 89581-38-4, molecular formula is C6H5BrN2O2, 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.

Under nitrogen, compound 1 (275 mg, 1.48 mmol), methyl-5- bromopyrimidine-2-carboxylate (165 mg, 0.76 mmol), Ruphos (33 mg, 0.07 mmol), Pd2(dba)3 (17 mg, 0. 018mmol) and Cs2C03 (748 mg, 2.29 mmol) were combined in toluene (8 mL) and heated to 100 C overnight. The crude residue was purified by preparative TLC (silica gel, GF254 10-40u, 25*25cm) with petroleum ether/EtOAc (1 :1 ) to afford Compound 2 as a white solid (80mg, 40%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89581-38-4, its application will become more common.

Reference:
Patent; REGENACY PHARMACEUTICALS, LLC; VAN DUZER, John H.; MAZITSCHEK, Ralph; BLUM, Charles; JARPE, Matthew B.; (53 pag.)WO2020/76951; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Application of 74840-38-3, 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 74840-38-3 as follows.

A solution of 5-bromo-2-methylthio-pyrimidine-4-carboxylic acid ethyl ester (100 mg, 0.36 mmol ; prepared from 5-bromo-2-methylthio-pyrimidine-4-carboxylic acid according to Coll. Czech. Chem. Commun. 1980, 45(2), 539) in dichloromethane (5 ml) was stirred at 0 C. under argon atmosphere and a solution of 3-chloroperbenzoic acid (178 mg, 0.72 mmol) in dichloromethane (5 ml) was added slowly. After continuous stirring for 30 min and warming-up to r.t., stirring was continued for another 6 h. The reaction mixture was partitioned between dichloromethane and sodium bicarbonate (saturated aqueous solution) and extracted. The organic phase was washed with water, dried and the solvent was evaporated. The product was obtained after purification by silica gel chromatography using a heptane /ethyl acetate gradient as colorless waxy solid (86 mg, 77%). MS: M=309.0 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74840-38-3, its application will become more common.

Reference:
Patent; Bleicher, Konrad; Flohr, Alexander; Groebke Zbinden, Katrin; Gruber, Felix; Koerner, Matthias; Kuhn, Bernd; Peters, Jens-Uwe; Sarmiento, Rosa Maria Rodriguez; US2011/306589; (2011); 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. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C6H4ClN3

Preparation 1; The solution of 5-chloropyrazolo [ 1, 5-a] pyrimidine (200 mg) and trans-4-methoxycyclohexanamine (168 mg) in isopropylalcohol(2 ml) was refluxed for 3 hours. After cooling to ambient temperature, the reaction mixture was poured into water, then extracted with ethyl acetate . The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel EPO elupsilonting with chloroform/methanol ( 100 : 0 to 100:10) to give N- (trans-4-methoxycyclohexyl)pyrazolo [1, 5-a] pyrimidin-5- amine (70 mg) .1H-NMR (DMSO-d6) 5:1.13-1.34 (4H,m) ,1-91-2.08 (4H,m) , 3.09-3.20 ( IH, m) ,3.33 (3H,s) , 3.70-3.86 (lH,m) ,5.95 (IH, d, J=2. OHz) ,6.19 (IH , d, J=7.6Hz) , 7.26(lH,d, J=7.4Hz) ,7.74 ( IH, d, J=2. OHz) , 8.41 (IH, d , J=7.6 Hz) . MS:247 (MH-H)+.

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, 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/13673; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 160199-05-3, 2,4-Dichlorobenzo[4,5]thieno[3,2-d]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, 160199-05-3, blongs to pyrimidines compound. Computed Properties of C10H4Cl2N2S

General procedure: 2,4-dibromopyrimidine (CAS Registry Number: 3921-01-5) (24.46 g, 102.82 mmol) was added to a round bottom flask and dissolved in THF (360 ml)4,4,5,5-tetramethyl-2- (naphthalen-1-yl-ethyl) -1,3,2-dioxaborolane(CAS Registry Number: 1280709-91-2) (29.54 g, 113.11 mmol),Pd (PPh3) 4 (4.75 g, 4.11 mmol),K2CO3 (42.63 g, 308.47 mmol) and water (180 ml) were addedAnd stirred at 90 C.After the reaction was completed, the reaction mixture was extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 18.03 g (yield: 60%) of the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,160199-05-3, its application will become more common.

Reference:
Patent; Duksan Neolux Co.,Ltd.; Song Hyeon-ju; Park Mu-jin; Jeong Ho-yeong; Lee Mun-jae; Lee Seon-hui; Kwon Jae-taek; (49 pag.)KR2018/97955; (2018); A;,
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