Month: December 2020

705-24-8 , The common heterocyclic compound, 705-24-8, name is 4,6-Dichloro-2-(trifluoromethyl)pyrimidine, molecular formula is C5HCl2F3N2, 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 solution of 4,6-dichloro-2-(trifluoromethyl)pyrimidine (800 mg, 3.7 mmol) in 2 mL of DMSO were added L-proline t-butylester (660 mg, 3.7 mmol) and DIEA (1.3 mL, 7.4 mmol). The mixture was heated at 90C in a microwave for one hour. After cooling, 4-(3-carboxypropyl)piperidine hydrochloride (770 mg, 3.7 mmol) and DIEA (650 mu, 3.7 mmol) were added, and the reaction was heated at 120C for three hours. EtOAc was added and the solution was washed with IN HCl and brine, dried Na2S04), concentrated in vacuo, and purified via silica gel chromatography (0-5% MeOH/DCM) to afford Compound 29A (1.3 g, 72%). LCMS (method A): m/z 487.3 (M+H)+.

According to the analysis of related databases, 705-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; MCGUINNESS, Brian F; XU, Xiaoqing; KULTGEN, Steven G.; MCMASTER, Ellen Sieber; BEASLEY, James R.; (356 pag.)WO2018/5794; (2018); A2;,
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 74-69-1, name is 2-Methyl-4-pyrimidinamine. This compound has unique chemical properties. The synthetic route is as follows. 74-69-1

Example 58: (R)-l-[(2-Methyl-pyrimidin-4-ylcarbamoyl)-methyl]-3-(l-phenyl- cycloheptanecarbonyloxy)-l-azonia-bicyclo[2.2.2]octane chloridea) 2-Chloro-N-(2-methyl-pyrimidin-4-yl)-acetarnideH,ISLCl 2-Methyl-pyrimidin-4-yl amine (545 mg) was suspended in DCE (5 niL) and chloroacetylchloride (0.4 mL) was added dropwise. The reaction was heated in a microwave at 8O0C for 5mins. The reaction mixture was cooled to give a solid that wa ftered, washed with dichloromethane then suspended in dichloromethane and sat. NaHCO3 (aq) was added. The organic phase was collected and the aqueous layer ext? with dichloromethane (x2). The combined organic layer was dried over sodium sulphc and concentrated. The crude product was purified by silica gel chromatography elutinj with 0-10%MeOH/dichloromethane to give the sub-titled compound as a yellow solid mg, 7.5 %).1H NMR (400 MHz, DMSO-D6): delta 1 1.16 (s, IH), 8.58 (d, IH), 7.84 (d, IH), 4.37 (s, 2.53 (s, 3H).

Statistics shows that 74-69-1 is playing an increasingly important role. we look forward to future research findings about 2-Methyl-4-pyrimidinamine.

Reference:
Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

130049-82-0, 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. 130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one. This compound has unique chemical properties. The synthetic route is as follows.

Example 3 Preparation of Compound of Formula (I) PaliperidoneIn a three necked flask acetonitrile (230 ml), compound (IV) (20 g) and compound (VI) (23.3 g) were charged. To the reaction mass, potassium carbonate (18 g) and potassium iodide (0.5 g) were added. The contents were heated to 76-78 C. and maintained for 3 hours at 76-78 C. After completion of reaction, the reaction mixture was cooled to 0-5 C. and stirred for 1 hour. The solid, was filtered, washed with water (65 ml). The solid obtained was dissolved in methanol (190 ml) by heating the contents to 60-65 C., treated with activated charcoal (3.5 gm), stirred at 60-65 C. for 30 minutes. The reaction mass was filtered hot over hyflo at 60-65 C., washed with hot methanol (20 ml). Methanol was distilled completely under vacuum below 45 C. to obtain residue. Ethyl acetate (20 ml) was charged and continued distillation under vacuum to remove traces of methanol. The residue was stirred in (20 ml) ethyl acetate for 1 hour at 25-30 C. The resulting solid was filtered and washed with ethyl acetate (10 ml) and dried under vacuum at 40-45 C. for 6 hours to yield 6.5 g of paliperidone. (HPLC purity-99.5%).

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 130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one.

Reference:
Patent; CIPLA LIMITED; US2010/298565; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

504-17-6 , The common heterocyclic compound, 504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, 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.

General procedure: To a mixture of an aromatic aldehyde (0.25 mmol), 2-thiobarbituric acid(0.5 mmol), ammonium acetate (0.3 mmol), [H-NMP]+[HSO4]- (12 mol%)and water (2 ml) was added. Then, ultrasonic probe was directly immersed inthe resulting mixture. The progress of the reactions was monitored by TLCuntil conversion of the starting materials was satisfactory. After completion ofthe reaction, the solvent was evaporated and the precipitate was washed withEtOH and hot water to afford the pure product. All products were identified byphysical and spectroscopic data. The synthesis of the compounds 4b and 4j wasinvestigated but unfortunately even after 24 h, only a trace amount of productwas observed by TLC, that is why we could not reported the spectroscopic dataof them.

The synthetic route of 504-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naeimi, Hossein; DIdar, Asieh; Rashid, Zahra; Zahraie, Zohreh; Journal of Antibiotics; vol. 70; 7; (2017); p. 845 – 852;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

588-36-3, 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 588-36-3, name is 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To the solution of 4-amino-5-hydroxymethyl-2-(methylthio)pyrimidine (1-1; 1.0 g, 5.84 mmol) in CHC13 (100 mL) was added Mn02(2.5 g, 29.2 mmol, 5 equiv). The suspension was stirred at rt overnight. The mixture was filtered through celite and washed with CHC13. The combined filtrate was concentrated to give the titled compound (1-2). ?H-NMR (500 MHz, CDCI3) 8 9.78 (s, 1H), 8.42 (s, 1H), 8.20 (broad, 1H), 5.74 (broad, 1H)), 2.55 (3,3H).

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 588-36-3, 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine.

Reference:
Patent; MERCK & CO., INC.; WO2005/100356; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

588-36-3, Adding a certain compound to certain chemical reactions, such as: 588-36-3, 4-Amino-5-hydroxymethyl-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, 588-36-3, blongs to pyrimidines compound.

(3) To a suspension of the compound (2.52 g) obtained in (2) above in chloroform (70 ml) is added manganese dioxide powder (7.56 g), which is three-fold amount compared to the starting material, and the mixture is stirred vigorously at room temperature overnight. The insoluble substances are removed by filtration, and the filtrate is concentrated in vacuo to obtain a colorless solid, which is extremely insoluble in an organic solvent. The resultant solid is recrystallized from a mixed solution of chloroform and methanol, triturated with a mixed solvent of chloroform-diisopropyl ether-hexane, washed with diisopropyl ether and hexane to give 2-methylthio-5-formyl-4-aminopyrimidine (1.75 g) as colorless powder. M.p. 186-187 C, MS (m/z): 170 (MH+). IR(nujol): 3406, 3289, 3177, 1667, 1631, 1616, 1585, 1529, 1387, 1180, 781 cm-1 .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,588-36-3, its application will become more common.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1364950; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

109-12-6, 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. 109-12-6, name is Pyrimidin-2-amine. A new synthetic method of this compound is introduced below.

General procedure: To a solution of theappropriate amine (31-44, 10 mmol) and triethylamine (10 mmol) in anhydrous chloroform was added dropwisechloroacetylcloride (30, 12 mmol) at0-5 C and the mixture was stirred for 12 h at the same temperature under N2.Then the solvent was removed under vacuum, and the residue dissolved in ethylacetate was once washed with water. The organic phase was stirred with 10%activated charcoal for 30 min and filtered through a neutral alumina bed.Finally, the solvent was distilled under vacuum. It is worth mentioning thatall the products obtained decompose rapidly, therefore they were used immediatelyin the next reaction.

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. 109-12-6, Pyrimidin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Velazquez-Lopez, Jose Miguel; Hernandez-Campos, Alicia; Yepez-Mulia, Lilian; Tellez-Valencia, Alfredo; Flores-Carrillo, Paulina; Nieto-Meneses, Rocio; Castillo, Rafael; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4377 – 4381;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

109-12-6 , The common heterocyclic compound, 109-12-6, name is Pyrimidin-2-amine, molecular formula is C4H5N3, 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 1 L flask was charged with 40 g (0.42 mol) of 2-aminopyrimidine and 840 mL of acetonitrile / 84 mL of DCM was added, and 78.6 g (0.44 mol) of NBS (N-bromosuccinimide) was added thereto at a temperature of 5 C for 4 times. The temperature was gradually raised to room temperature and stirred for 24 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, 1000 mL of water and 1000 mL of DCM were added, and the mixture was stirred for 2 hours. The separated organic layer was washed with 500 mL of brine, dried over anhydrous Na2SO4, and concentrated. The concentrate was recrystallized under DCM / Hexane conditions to give 67.5 g (yield: 92.4%) of a compound as a white solid (Intermediate (19)).

According to the analysis of related databases, 109-12-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lapto Co., Ltd.; MOON, Seong-shik; SEOK, Moon-ki; GO, Byung-soo; KIM, Nam-ho; KWAK, Se-young; HAN, Gab-jong; OH, Eu-gene; (38 pag.)KR2017/103574; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

696-82-2 ,Some common heterocyclic compound, 696-82-2, molecular formula is C4HF3N2, 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.

(3) N-(4-((4-(4,6-Difluoropyrimidin-2-yl)piperazin-1-yl)methyl)-phenylmethyl)acetamide To a solution of 2,4,6-trifluoropyrimidine (1.4 g) and potassium carbonate (2.1 g) in acetonitrile (30 ml) was added a solution of N-(4-((piperazin-1-yl)methyl)phenylmethyl)acetamide (2.5 g) in acetonitrile (20 ml) over 5 min under ice-cooling. The mixture was stirred at the same temperature for 1.5 hr. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a white solid (3.2 g). The obtained white solid was purified by silica gel column chromatography (developing solvent; chloroform_methanol=50:1) to give a crude purification product (1.3 g) of N-(4-((4-(4,6-difluoropyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide and a crude purification product (1.1 g) of N-(4-((4-(2,6-difluoropyrimidin-4-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide. The crude purification product of N-(4-((4-(4,6-difluoropyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide was crystallized from ethyl acetate:diisopropyl ether to give the title compound (1.0 g) as white crystals, m.p.=128-129 C. 1H-NMR(CDCl3)delta: 2.03(3H, s), 2.46(4H, t, J=5.3 Hz), 3.52(2H, s), 3.79(4H, t, J=5.3 Hz), 4.43(2H, d, J=5.3 Hz), 5.66(1H, t, J=1.3 Hz), 5.75(1H, brs), 7.23-7.32(4H, m); IR(KBr): 3288, 2918, 1635, 1552 cm-1; MS(EI): 361(M+); Elemental analysis: Calculated: C; 59.82, H; 5.86, N; 19.38; Found: C; 59.83, H; 5.85, N; 19.44.

According to the analysis of related databases, 696-82-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Pharma Corporation; US6455528; (2002); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

302964-08-5 , The common heterocyclic compound, 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, 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 20; Procedure for the Preparation of Dasatinib Form A1A mixture of compound 1 (394.3 mg, 1 mmol), N-(2-hydroxyethyl)piperazine (390.6 mg, 3 mmol) and N-ethyldiisopropylamine (0.348 ml, 2 mmol) in DMF (1 ml) was stirred at 100 C. for 2.5 h. Isopropyl alcohol (10 ml) was slowly added through a condenser and mild reflux was maintained for 10 min. The suspension was cooled to room temperature. The product was filtered after 1 hour and washed with i-PrOH (3¡Á) and dried on the filter. Yield: 370 mg.Example 29Procedure for the Preparation of Dasatinib Form A1A mixture of compound 1 (1.5 mmol), N-(2-hydroxyethyl)piperazine (3 mmol) and N-ethyldiisopropylamine (3 mmol) in DMF was stirred at 100 C. for 4 h, i-propanol was added at this temperature. The suspension was slowly cooled to 0-5 C. The product was filtered off, washed by i-propanol and dried on the filter.

According to the analysis of related databases, 302964-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIMO, Ondrej; Filipcik, Jiri; Martaus, Alexandr; Jegorov, Alexandr; Gavenda, Ales; Aronhime, Judith; Vraspir, Pavel; Koltai, Tamas; Faustmann, Jiri; Gabriel, Roman; US2009/118297; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia