Month: September 2021

Related Products of 1194-78-1, 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 1194-78-1 as follows.

(D) 7-Chloro-1H-1,2,3-triazolo[4,5-d]pyrimidin-5-amine A solution of 6-chloro-2,4,5-pyrimidinetriamine (10.94 g, 0.0686 mol) and isoamyl nitrite (9.20 ml, 0.0686 mol)in dioxane (500 ml, freshly purified by passage through basic alumina) was heated under nitrogen with stirring for 2 hours at 90. The reaction mixture was cooled, treated with activated carbon, filtered, and concentrated to 150 ml. Petroleum ether (250 ml, bp 35-60) was added. The precipitate was filtered, washed the petroleum ether (50 ml) and dried in vacuo over P2 O5 at 40 for 16 hours to give 9.23 g of crude desired product which was then used in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1194-78-1, its application will become more common.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US5126345; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1, 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. 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, 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.

Into a round bottom flask the catalyst PdCl2(dppf), under an atmosphere of nitrogen, was placed with 15 mL of toluene along with a stir bar. A suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 1.47 g, 9.57 mmol) in 15 mL of toluene was added at room temperature. After stirring for 10 minutes, methylmagnesium bromide (17.00 mL, 3.00 M in ether, 51.00 mmol) was added dropwise. The solution turned from orange to yellow, and was slowly heated to 60 C. and stirred for 3 hrs at 60 C. and then overnight at room temperature. The resulting dark orange reaction mixture was quenched with 1 N hydrochloric acid and adjusted to pH~5, then extracted with ethyl acetate and water saturated with sodium chloride. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluding with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a yellow solid (42, 202 mg). 1H-NMR(dmso-d6) was consistent with the desired compound. MS(ESI) [M+H+]+=134.3.

According to the analysis of related databases, 3680-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Plexxikon, Inc.; US2009/286783; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 54326-16-8 , The common heterocyclic compound, 54326-16-8, name is 5-Chloropyrimidin-2(1H)-one, molecular formula is C4H3ClN2O, 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 25 5-Chloro-1-(4-cyanophenacyl)pyrimidin-2-one A suspension of 5-chloropyrimidin-2-one (412 mg) and 2-bromo-4′-cyanoacetophenone (677 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for one hour. Water (100 ml) was added and the collected solid was crystallized from ethyl acetate to give the title pyrimidinone (375 mg,); m.p. 236-240; lambdamaxEtOH 248 nm (epsilon 26140), 289 nm (epsilon 2130), lambdainf 254 (epsilon 22800).

The synthetic route of 54326-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Group Limited; US4636509; (1987); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4319-77-1, 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 4319-77-1 as follows.

C. Preparation of 4,6-dimethoxy-5-(pyridin-4-yl)pyrimidine A mixture of 5-bromo-4,6-dimethoxypyrimidine (2.18 g, 10 mmol), pyridine-4-boronic acid (1.85 g, 15 mmol), K2CO3 (2.76 g, 20 mmol), and PXPd (539 mg, 1.0 mmol) in ethanol/THF (1:1, 25 mL) under argon was heated at 70 C. for 3 h. Analysis by HPLC/MS indicated that the reaction was complete. After the reaction mixture was cooled to room temperature, the solvent mixture was removed under reduced pressure. The residue was dissolved in EtOAc (30 mL) and washed with saturated aqueous NaCl (20 mL), then dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography eluted with ethyl acetate-hexanes to obtain the title compound (1.79 g) as a white solid. 1H NMR (CDCl3): delta 3.97 (s, 6H), 7.36 (d, 2H), 8.47 (s, 1H), 8.64 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4319-77-1, its application will become more common.

Reference:
Patent; Wu, Gang; Mikkilineni, Amarendra B.; Sher, Philip M.; Murugesan, Natesan; Gu, Zhengxiang; US2006/287341; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 89581-38-4, 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.89581-38-4, name is Methyl 5-bromopyrimidine-2-carboxylate, molecular formula is C6H5BrN2O2, molecular weight is 217.0201, as common compound, the synthetic route is as follows.

To the reaction flask were added 1 mmol of compound F55, N, N-dimethylglycine, cuprous iodide, Cs2CO3, 1, 4-Dioxane and 2 mmol of 5-bromo-2-pyrimidinecarboxylic acid methyl ester, heating under nitrogen to 80 C for 24 h,Water, extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified on a silica gel column(Eluent: petroleum ether: ethyl acetate = 1: 1) to give the title product as a pale yellow oily liquid.

The chemical industry reduces the impact on the environment during synthesis 89581-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangdong Zhongsheng Pharmaceutical Co., Ltd.; Chen, Lijuan; Long, Chaofeng; Chen, Xiaoxin; Liu, Zhuowei; Ye, Haoyu; Xie, Chengshi; (104 pag.)CN106045923; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1421372-67-9, 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 1421372-67-9, name is N1-(2-(Dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-2-nitrobenzene-1,4-diamine. This compound has unique chemical properties. The synthetic route is as follows.

1) Weigh 200g of the raw material hydrogenation precursor nitro compound, and then add it to a mixture of 4L of methanol and 100g of concentrated hydrochloric acid, stir and dissolve, then add 10g of Pd/C catalyst with Pd content of 10%, stir well and mix to form Material I, the material I is sent to the preheating module 1 of the microchannel reactor for preheating, and after preheating, enters the reaction module group of the microchannel reactor.2) The reaction module group that delivers hydrogen to the microchannel reactor and the step 1) the preheated material I reacts in the reaction module group, wherein: the flow rate of the slurry pump is adjusted so that the flow rate of the material I is 40.0 g/min. The flow rate of the H2 gas flow meter is adjusted to 500 ml/min, the molar ratio of the raw material hydrogenation precursor nitro compound to hydrogen is 1:3.5, the reaction temperature is 90 C, the temperature of the cooling module is 20 C, and the residence time of the reaction is 25s, the reaction pressure is 1.5Mpa, and the collection flows out from the outlet of the cooling module.The reaction solution is subjected to post-treatment, which means that the catalyst is recovered by filtration, and the solvent is distilled off under reduced pressure. The residue is added to 1 L of water, stirred and dissolved, and the pH of the system is adjusted to 9.0 by a NaOH solution having a mass fraction of 20%. 10.0, then join500ml of ethyl acetate was extracted and separated, the organic phase was discarded, the aqueous phase was stirred and crystallized at 10 C for 1 hour, filtered, and the product was washed with a small amount of ethanol, and vacuum dried at 50 C for 8 hours to obtain an oxetinib intermediate. Target product 160.65g, yield85.73%, purity 99.68%.

According to the analysis of related databases, 1421372-67-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Heilongjiang Xinchuang Bio-technology Development Co., Ltd.; Ren Jiqiu; Yang Kun; Li Haitao; (12 pag.)CN108484579; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1193-24-4, 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. 1193-24-4, name is 4,6-Dihydroxypyrimidine. A new synthetic method of this compound is introduced below.

EXAMPLE 2 4,6-Dihydroxypyrimidine (20.5 g) was dispersed with agitation in dichloromethane (400 ml). Dimethylaniline (40.4 g) was added to the agitated mixture and the system was sealed (except for a vent line to a scrubber). Phosgene gas (56 g) was introduced from a cylinder and condensed onto a cold finger and collected in a pressure equalised dropping funnel. Once collected, the phosgene liquid was added to the reaction mixture over 15 minutes. The mixture was heated and agitated at reflux (29 C. approximately) for 17 hours after which time the mixture was cooled to room temperature and the excess phosgene removed by sparging with nitrogen. Water (400 ml) was added slowly to the agitated reaction mass with cooling to maintain the temperature at ambient. The organic layer was separated, and the aqueous was then extracted with dichloromethane (2*100 ml). The combined extracts were dried over anhydrous sodium sulphate and concentrated by rotary evaporation to give 4,6-dichloropyrimidine as an orange crystalline solid (27 g), equivalent to a yield of 80% (hplc analysis).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-24-4, its application will become more common.

Reference:
Patent; Zeneca Limited; US5750694; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 58347-49-2, 7-Chloropyrazolo[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, Safety of 7-Chloropyrazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Safety of 7-Chloropyrazolo[1,5-a]pyrimidine

EXAMPLE 18N-r(35r)-l-{7-Fluoro-8-methyl-3-r(15r)-l-(pyrazolorL5-alphalpyrimidin-7-ylamino>;)ethyl1- quinolin-2-vUpyrrolidin-3-yl]cyclopropanecarboxamide(5)-(-)-3 -Amino- 1-pyrrolidinecarboxylic acid tert-butyl ester (500 mg, 2.68 mmol), DCM (30 mL), DIPEA (2 mL) and cyclopropanecarbonyl chloride (0.275 mL, 3 mmol) were combined at r.t. under a nitrogen atmosphere. The reaction mixture was stirred for 1 day, then diluted with DCM (50 mL) and washed with water (50 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo to give a brown oil. This oil, MeOH (10 mL) and 2N HCl in Et2O (5 mL) were stirred at r.t. for 3 days. The reaction mixture was then concentrated in vacuo. The resulting material, Intermediate 15 (500 mg, 1.48 mmol), H-BuOH (16 mL) and DIPEA (2 mL) were combined in a sealed tube and heated to 13O0C for 15 days. The reaction mixture was cooled, concentrated onto silica and purified by column chromatography (SiO2, 0-100% EtOAc in isohexane) to give a tan solid. This material, MeOH (10 mL) and 2N HCl in Et2O (7 mL) were combined and stirred at r.t. for 24 h. The reaction mixture was concentrated to give a brown glass. A portion of this material (50 mg, 0.127 mmol), n- BuOH (6 mL), DIPEA (1 mL) and 7-chloropyrazolo[l,5-alpha]pyrimidine (50 mg, 0.25 mmol) were combined in a sealed tube and heated under microwave irradiation to 16O0C for 2 h. The reaction mixture was then concentrated to dryness and purified by preparative HPLC to give the title compound (32.3 mg, 54%) as a brown glass. 6H (DMSO-d6) 8.44 (IH, d, J6.91 Hz), 8.38 (IH, d, J6.91 Hz), 8.25 (IH, s), 8.17 (IH, d, J 2.27 Hz), 8.10 (IH, d, J5.21 Hz), 7.57 (IH, dd, J8.84, 6.41 Hz), 7.10 (IH, t, J9.10 Hz), 6.49 (IH, d, J2.27 Hz), 6.06 (IH, d, J 5.28 Hz), 5.27 (IH, m), 4.50-4.42 (IH, m), 4.07- 3.94 (2H, m), 3.82-3.74 (IH, m), 3.60 (IH, dd, J 10.47, 5.21 Hz), 2.51 (3H, s), 2.32-2.23 (IH, m), 2.04-1.94 (IH, m), 1.77 (3H, d, J6.54 Hz), 1.66-1.58 (IH, m), 0.77-0.67 (4H, m). LCMS (ES+) 474 (M+H)+, RT 2.51 minutes {Method I).

The synthetic route of 58347-49-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; LANGHAM, Barry, John; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2010/133836; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, molecular weight is 95.1, as common compound, the synthetic route is as follows.Computed Properties of C4H5N3

General procedure: A solution of Pd(OAc)2 and BINAP in dry toluene was warmed at 45 C for 5 min. The leaving group-containing purine was then added under N2 bubbling; the mixture was kept at 45 C for 10 min. and KOtBu was added. After 10 min, the appropriate nucleophile was added. The mixture was heated at 100 C under N2 until reaction completion (3 h to 2 days depending upon the nucleophile used). After cooling to room temperature,the mixture was filtered through Celite, and concentrated. The residue was dissolved in CH2Cl2 (75 mL) and washed (1 × 10 mL) with water and brine (2 × 10 mL). The organic layer was dried and concentrated under vacuum. The residue was purified by chromatography on silica gel using various amounts of EtOAc/cyclohexane/ethanol as eluants.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,591-55-9, 5-Aminopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Houz, Sandrine; Hoang, Nha-Thu; Lozach, Olivier; Le Bras, Jacques; Meijer, Laurent; Galons, Herv; Demange, Luc; Molecules; vol. 19; 9; (2014); p. 15237 – 15257;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 32779-37-6 , The common heterocyclic compound, 32779-37-6, name is 2,5-Dibromopyrimidine, molecular formula is C4H2Br2N2, 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.

11126] To a solution of intermediate B-S (520 g, 2.45 mmol) in DMA (8.2 mE) was added DIPEA (0.84 mE, 4.90 mmol) followed by 2,5-dibromopyrimidine (661 g, 2.69 mmol). The reaction mixture was heated at 120 C. for 30 minutes using microwave and was then diluted with water and EtOAc. The aqueous phase was extracted twice with EtOAc and the combined organic layers were washed with a saturated solution of NaC1, dried over Mg504, filtered and evaporated. Purification via silica gel chromatography (0-40% EtOAc in hexanes) gave the title compound (651 g, 72%). MS (ESI): mass calcd. for C,5H2,BrN4O2, 368.1; m/z found, 370.9 [M+H]. ?H NMR (500 MHz, CDC13) oe 8.28 (is, 2H),5.56 (s, 1H), 4.29 (s, 1H), 4.23-4.15 (m, 1H), 3.99-3.91 (m, 1H), 2.03-1.93 (m, 1H), 1.87-1.63 (m, 2H), 1.62-1.32 (m, 12H).

The synthetic route of 32779-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; COATE, Heather R.; DVORAK, Curt A.; FITZGERALD, Anne E.; LEBOLD, Terry P.; PREVILLE, Cathy; SHIREMAN, Brock T.; (473 pag.)US2016/46640; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia