Tag: M.W:100-200

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.3001-72-7, name is 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine, molecular formula is C7H12N2, molecular weight is 124.1836, as common compound, the synthetic route is as follows.Safety of 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine

General procedure: The p-nitrophenyl carbonate derivative (0.3 g) was dissolved in AR grade THF (5 mL) at room temperature and DBU or DBN (2 equiv) was added. The temperature of the reaction mixture was raised to 60 C and stirring was continued for 1 h. After completion, the reaction mixture was extracted with ethyl acetate (2 × 30 mL), the organic layer washed with saturated NaHCO3 solution, water, brine and dried over anhydrous Na2SO4. Thesolvent was evaporated and the crude compound was purified by column chromatography

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3001-72-7, 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Vangala, Madhuri; Shinde, Ganesh P.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2086 – 2092;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4318-56-3, 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. 4318-56-3, name is 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C5H5ClN2O2, 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.

3-Methyl-6-chloro uracil (12 g, 76 mmol),Compound 3 (17.2 g, 80 mmol) and K2CO3 (10 g,80 mmol) in DMSO (100 mL) was stirred for 2 h and the reaction was diluted with water and extracted with EtOAc. The organic phase was dried over MgSO4 and the solvent was removed. Purification by column chromatography gave 4,13.2 g (60% yield).

According to the analysis of related databases, 4318-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Institute of Pharmaceutical Industry; China Pharmaceutical Industry Research Institute; Chen, Wu; Liu, Xiangkui; Ji, Zhongde; Zhu, Xueyan; Yuan, Zhedong; (10 pag.)CN105418580; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 57489-77-7, 5,7-Dichloropyrazolo[1,5-a]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, Computed Properties of C6H3Cl2N3, blongs to pyrimidines compound. Computed Properties of C6H3Cl2N3

Example 3; [A General Procedure for the Synthesis of a Pyrazolo[1,5-a]pyrimidine Derivative Represented by General Formula (V-04)]; A mixture was prepared by adding N-chlorosuccinamide, N-bromosuccinamide or iodine monochloride (0.011 mol) to a chloroform (50 mL) solution containing 5,7-dichloropyrazolo[1,5-a]pyrimidine (V-03) (0.01 mol) at room temperature. The mixture was stirred under heating and reflux until all solid was dissolved and the starting materials disappeared by TLC. The mixture was poured into ice/water to separate the organic layer, which was washed with aqueous Na2CO3 solution, subsequently dried with MgSO4, and the solvent was removed under vacuum. The residue was purified by silica gel chromatography to obtain 3-halo-5,7-dichloropyrazolol,5-alpyrimidine (V-04). The typical yield of the reaction ranged from 60 to 90%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57489-77-7, 5,7-Dichloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; TEIJIN PHARMA LIMITED; US2006/135514; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10132-07-7, 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 10132-07-7, name is 4-Amino-2,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

N-tert-Butoxycarbonylpiperidinyl-4-methylamine (5.0 g) was slowly added to a stirred solution of 2,4-dichloro-6-aminopyrimidine (5.7 g) in 1-pentanol (20 mL). The solution was stirred at 120 C. for 12 hours. The solution was then concentrated and the resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/9) to give Intermediate 224-I (3.6 g) in a 45% yield. Intermediate 224-I (2.4 g) was then dissolved in CH2Cl2 (80 mL) and 20% TFA/CH2Cl2 (20 mL) was added. The solution was stirred at room temperature overnight. The solution was then concentrated and the resultant residue was purified by column chromatography on silica gel (21% NH3 (aq)/MeOH=1/19) to afford Intermediate 224-II (1.5 g) in a 90% yield. Intermediate 222-III (3.3 g) prepared in Example 222 was added to a solution of Intermediate 224-II (1.9 g) in MeOH (40 mL). The mixture was stirred at 60 C. for 12 hours. NaBH4 (0.3 g) was then added at 0 C. After the mixture was stirred for 1 hour, an aqueous solution of NH4Cl (10%, 10 mL) was added. The mixture was extracted with EtOAc, dried over anhydrous MgSO4, and filtered. The solution thus obtained was then concentrated. The resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/1) to afford Intermediate 224-III (1.5 g) in a 40% yield. N1-Morpholine-N1-piperazine ethane (370 mg) was added to Intermediate 224-III (300 mg) in 1-pentanol (1 mL). The mixture was stirred at 120 C. for 12 hours. After the solution was concentrated, the residue was treated with water and extracted with CH2Cl2. The organic layer was separated and concentrated. The resultant residue was purified by column chromatography on silica gel (EtOAc/Hexane=1/9) to afford Intermediate 224-IV (281 mg) in a 70% yield. A solution of 20% TFA/CH2Cl2 (3 mL) was added to a solution of Intermediate 224-IV (281 mg) in CH2Cl2 (2 mL). The reaction mixture was stirred for 8 hours at room temperature and concentrated by removing the solvent. The resultant residue was purified by column chromatography on silica gel (21% NH3 (aq)/MeOH=1/19) to afford Compound 224 (200 mg) in a 85% yield. Compound 224 was then treated with 1 M HCl (4 mL) in CH2Cl2 (2 mL) for 0.5 hours. After the solvents were removed, the residue was treated with ether and filtered to give hydrochloride salt of Compound 224. CI-MS (M++1): 544.4.

According to the analysis of related databases, 10132-07-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yen, Chi-Feng; Hu, Cheng-Kung; Chou, Ming-Chen; Tseng, Chen-Tso; Wu, Chien-Huang; Huang, Ying-Huey; Chen, Shu-Jen; King, Chi-Hsin Richard; US2006/281712; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 49844-90-8, 4-Chloro-2-(methylthio)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, 49844-90-8, blongs to pyrimidines compound. Recommanded Product: 49844-90-8

Bromo trimethylsilane (23 mL, 174.31 mmol) was addedto a solution of 4-chloro-2-methylsulfanylpyrimidine (2.9 g 25 mmol) inacetonitrile (240 mL).The mixture was stirred for 30 h at 40C. The reactionwas monitored by TLC. After cooling to room temperature, NaHCO3saturated solution (250 mL) was added and the product was extracted with AcOEt.The organic layer was dried over Na2SO4, filtered, andevaporated under reduced pressure. The crude residue was purified bychromatography on silica gel using dichloromethane-ethyl acetate (9:1).Evaporation of the eluent in vacuum gave the desired compound in 96% yield(4.66 g) as colorless oil. Litt 1H NMR (CDCl3): delta 2.56(s, 3H, SCH3), 7.16 (d,1H, J = 5.2 Hz, H-5pyrimidine),8.26 (d, 1H, J = 5.2 Hz, H-6pyrimidine).13CNMR (CDCl3): delta 2.56 (s, 3H, SCH3),7.16 (d, 1H, J = 5.2 Hz, H-5pyrimidine),8.26 (d, 1H, J = 5.2 Hz, H-6pyrimidine).HPLC:Rt = 3.11min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,49844-90-8, its application will become more common.

Reference:
Article; Bendjeddou, Lyamin Z.; Loaec, Nadege; Villiers, Benoit; Prina, Eric; Spaeth, Gerald F.; Galons, Herve; Meijer, Laurent; Oumata, Nassima; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 696 – 709;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 4212-49-1 ,Some common heterocyclic compound, 4212-49-1, molecular formula is C6H8N2O2, 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.

N, N-DIISOPROPYLETHYLAMINE (195 mL, 0.86 mol) (Aldrich) was added slowly to a mixture of 5-ethyl uracil (52.3 g, 0.37 mol) (from Example LC, suprn) and phosphorous oxychloride (150 mL, 1.61 mol) (Aldrich) with external cooling in a cold water bath. The mixture was heated at reflux for 3.8 hours and cooled to room temperature. Mixture was then poured into ice (300 g). Ethyl acetate (100 mL) was added and mixture stirred at 20 C for 30 minutes with cooling in an ice-water bath. The resulting mixture was filtered through CELITEE and the filtrate extracted with ethyl acetate-hexanes (1: 1,3 X 300 mL). The combined organic layers was washed with water (250 mL), dried over sodium sulfate, filtered and concentrated to dryness. This residue was dissolved in ethyl acetate- hexanes (1 : 1) and filtered through TLC grade silica gel and eluting with the same solvent. The filtrate was concentrated to dryness to give 2,4-dichloro-5-ethyl-pyrimidine. (Yield 56.3 g, 85.2%).

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. 4212-49-1, 5-Ethyluracil, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/41821; (2004); 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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, 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. name: 2-Chloro-4-(trifluoromethyl)pyrimidine

4-(2-Bromophenyl)piperazine-1-carboxylic acid tert-butyl ester (280 mg, 0.82 mmol),4,6-Dimethylpyrimidin-2-amine (151 mg, 1.23 mmol),Sodium tert-butoxide (0.16 g, 1.16 mmol), tris(dibenzylideneacetone) dipalladium (75 mg, 0.082 mmol) and(±)-2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl (102 mg, 0.164 mmol) was added to anhydrous tolueneIn (20 mL), the reaction was heated to 120 C for 12 hours under a nitrogen atmosphere. The reaction was stopped, and the mixture was cooled to room temperature. The mixture was poured into water (100 mL), ethyl acetate (40 mL×3), and the organic phase was combined and washed with water (50 mL) and brine (50 mL) Dry and distill off the solvent under reduced pressure.The obtained crude product was subjected to column chromatography (dichloromethane:methanol (V:V)=50:1)The title compound (white solid, 274 mg, 87%)

With the rapid development of chemical substances, we look forward to future research findings about 33034-67-2.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Guo Zhengjiang; (39 pag.)CN109912514; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 69034-12-4, 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. 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

Example 1.14: Preparation of 2-(4-(((lr,4r)-4-(5-(Methylsulfonyl)pyridin-2- yl)cyclohexyloxy)methyl)piperidin-l-yl)-5-(trifluoromethyl)pyrimidine (Compound 18).; To a dichloromethane (1 mL) solution of tert-butyl 4-(((lr,4r)-4-(5- (methylsulfonyl)pyridin-2-yl)cyclohexyloxy)methyl)piperidine-l-carboxylate (36 mg, 0.080 mmol), prepared in Example 1.13, Step B, was added a 4 M dioxane solution of hydrogen chloride (0.994 mL, 3.98 mmol). The reaction was stirred at 23 C for 30 min then concentrated. The residue was taken up in iPrOH (1.0 mL) and N-ethyl-N-isopropylpropan-2-amine (0.083 mL, 0.477 mmol). The resulting solution was divided into two equal portions. To one portion was added 2-chloro-5-(trifluoromethyl)pyrimidine (14.52 mg, 0.080 mmol). The reaction was stirred at 110 C for 40 min then concentrated. The residue was purified by preparative TLC (5% MeOH/CH2Cl2) to give the title compound (22.4 mg, 0.045 mmol, 113 % yield) as white solid. Exact mass calculated for C23H29F3N4O3S: 498.2, found: LCMS m/z = 499.5 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.18-1.26 (m, 2H), 1.34-1.44 (m, 2H), 1.60-1.70 (m, 2H), 1.85- 1.90 (m, 3H), 2.00-2.07 (m, 2H), 2.17-2.23 (m, 2H), 2.77-2.85 (m, 1H), 2.90-2.97 (m, 2H), 3.10 (s, 3H), 3.25-3.34 (m, 1H), 3.38 (d, = 6.0 Hz, 2H), 4.84-4.88 (m, 2H), 7.36 (d, = 8.2 Hz, 1H), 8.13 (dd, = 8.2 and 2.4 Hz, 1H), 8.46 (s, 2H), 9.05 (d, = 2.4 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,69034-12-4, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 90905-33-2 ,Some common heterocyclic compound, 90905-33-2, molecular formula is C6H6N2O, 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.

4-chloro-N2-methylpyridine-2, 3-diamine (840 mg, 5.33 mmol) and iron (III) chloride hexahydrate (360 mg, 1.33 mmol) were dissolved in DMF (26 ml). 2-Methylpyrimidine-5-carbaldehyde (716 mg, 5.86 mmol) was then added and the reaction was allowed to stir vigorously at 80 open to air for 18 h The reaction mixture was then diluted with 3:. 1 chloroform: IPA and washed with water The combined organic layers. were washed with brine, dried over MgSO 4, and concentrated in vacuo while loading onto silica gel Purification by column chromatography. (silica gel, eluting with a gradient of 0 -60percent 3: 1 EtOAc: EtOH in hexanes) gave 7-chloro -3-ethyl-2- (2- methylpyrimidin-5-yl) -3H-imidazo [4, 5-b] pyridine (Intermediate IV). MS ESI calc’d. for C 13 H 13 ClN 5 [M + 1]+ 274; found 274.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90905-33-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; ZHOU, Hua; KATZ, Jason D.; YANG, Lihu; METHOT, Joey; LIPFORD, Kathryn Ann; XU, Shimin; FU, Ning; XU, Guoquan; BIAN, Deqian; FU, Jianmin; LI, Yabin; FONG, Kin Chiu; (124 pag.)WO2017/125; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 22536-61-4, 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.22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

In a sealed glass tube a suspension of l-cyclopropyl-6-(lH-imidazol-5-yl)-3,3-dimethylindolin- 2-one (example 71a, 70 mg), 2-chloro-5-methylpyrimidine (37.0 mg) and cesium carbonate (158 mg) in acetonitrile (1.05 ml) was heated to 120 °C for 30 minutes under microwave irradiation. Then again 18 mg 2-chloro-5-methylpyrimidine and 89 mg cesium carbonate were added and the reaction mixture heated to 120°C under conventional heating for 2 hours. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel, gradient, 0percent to 100percent EtOAc in n-heptane). The title compound was obtained as off white solid (75 mg, 80percent). MS (ESI, m/z): 360.2 [(M+H)+].

Statistics shows that 22536-61-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-methylpyrimidine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia