Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 74502-83-3, 2-(Chloromethyl)-4,6-dimethylpyrimidine, 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, COA of Formula: C7H9ClN2, blongs to pyrimidines compound. COA of Formula: C7H9ClN2

A room temperature solution of 6-( i-methyl-i H-pyrazol-4-yl)-4-(6-(piperazin- 1- yl)pyridin-3 -yl)pyrazolo[ 1,5 -a]pyridine-3 -carbonitrile dihydrochloride (Example 2; 0.018 g, 0.0394 mmol) in dry DMF (0.3 mL) and TEA (54.9 tL, 0.394 mmol) was treated with 2-(2- bromoethoxy)propane (0.0197 g, 0.118 mmol). The reaction mixture was stirred overnight at 75C, and then additional 2-(2-bromoethoxy)propane (1 eq) and TEA (1 eq) were added. The reaction mixture was allowed to stir 24 h at 75 C. After cooling to room temperature, the resulting reaction mixture was directly purified by C18 reverse phase chromatography (5-99 o ACNwater as the gradient eluent) to afford the title compound (7.4 mg, 41o yield). MS (apci) mz = 471.2 (M+H).used only 1.5 eq of the alkyl halide (2-(chloromethyl)-4,6-dimethylpyrimidine),10 eq of TEA, and was conducted at room temperature, but otherwise followed a similar procedure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,74502-83-3, 2-(Chloromethyl)-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; CHICARELLI, Mark J.; GOLOS, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; (594 pag.)WO2017/11776; (2017); 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.157335-97-2, name is 5-Bromo-4,6-dimethylpyrimidine, molecular formula is C6H7BrN2, molecular weight is 187.0372, as common compound, the synthetic route is as follows.Product Details of 157335-97-2

Under Ar(g), to a mixture of pyrazin-2-amine (1) (209mg, 2.2mmol), 5- bromo-4,6-dimethylpyrimidine (2) (374mg, 2.0mmol), Cs2C03 (1.30g, 4.0mmol) was added degassed dry 1 ,4-dioxane (13mL). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (92mg, 0.1 mmol) and Xantphos (127mg, 0.22mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt. EtOAc (15ml_), H20 (10mL) and brine (5mL) were added to the reaction mixture. The organic phase was separated and the aqueous phase was extracted with EtOAc (15ml_). The organic layers were combined and Pd-scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (43mg, 1 1 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,157335-97-2, 5-Bromo-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 63558-65-6 ,Some common heterocyclic compound, 63558-65-6, molecular formula is C4H2ClIN2, 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-amino-2,5-difluorophenol (0.190 g, 1.310 mmol) in DMF ( 10 mL) was added potassium ter/-butoxide (0.168 g, 1.497 mmol). The mixture was stirred at RT for 30 min. 4-Chloro-5-iodopyrimidine (0.30 g, 1.248 mmol) was added and the reaction mixture was heated at 80 C overnight. The reaction mixture was quenched with water and the solution was extracted with EtOAc (3x). The organic solution was washed with 5% aqueous lithium chloride solution and brine. The organics were dried over gS04, filtered, and concentrated. The crude was purified by silica gel column chromatography ( 10% to 50%EtOAc/hexane) to obtain 2,5-difluoro-4-(5-iodopyrimidin-4-yloxy)benzenamine (160 mg, 36.7%) yield) which was used for the next reaction. MS (ESI) m/z: 349.9 (M+H+).

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. 63558-65-6, 4-Chloro-5-iodopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; FLYNN, Daniel, L.; KAUFMAN, Michael, D.; WO2011/139891; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, 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 C5H4Cl2N4O, blongs to pyrimidines compound. Computed Properties of C5H4Cl2N4O

Intermediate 1 RRN 104-[2-Amino-6-chloro-5-(formylamino)pyrimidin-4-yl]piperazine-1-carboxylic acid tert-butyl ester [0221] To a suspension of N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (10.0 g, 48.3 mmol) in 1,4-dioxane (400 mL) were added N,N-diisopropylethylamine (12.7 mL, 72.5 mmol) and piperazine-1-carboxylic acid tert-butyl ester (9.8 g, 53.1 mmol). The mixture was stirred at 55 C. for 1 h. The solvent was removed in vacuo and the residue was partitioned between DCM and water. The aqueous phase was extracted with further DCM and the combined organic fractions were washed with brine, then dried (Na2SO4) and evaporated in vacuo to give the title compound (17.1 g, 100%) as a white solid. LCMS (ES+) 357.4 (M+H)+, RT 1.08 minutes (method 3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, and friends who are interested can also refer to it.

Reference:
Patent; Brookings, Daniel Christopher; Ford, Daniel James; Franklin, Richard Jeremy; Ghawalkar, Anant Ramrao; Kulisa, Claire Louise; Neuss, Judi Charlotte; Reuberson, James Thomas; US2014/315885; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1193-21-1, 4,6-Dichloropyrimidine, 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, Recommanded Product: 1193-21-1, blongs to pyrimidines compound. Recommanded Product: 1193-21-1

298 mL of methanol is added to 387 mL (7.98 mol) of hydrazine monohydrate, and the mixture is cooled to 10C (internal temperature). To this mixed solution is gradually added 149 g (1.00 mol) of 4,6-dichloropyrimidine (at an internal temperature of 20C or lower), then the ice bath is removed to increase the temperature to room temperature, followed by stirring at the same temperature for 30 minutes. Thereafter, the mixture is further heated to an internal temperature of 60C, and is stirred at the same temperature for 5 hours. After completion of the reaction, 750 ml of water is added thereto, and then the mixture is cooled to an internal temperature of 8C with ice. Crystals precipitated are collected by filtration, spray-washed with water, then spray-washed with isopropanol. The crystals are dried at room temperature for 36 hours to obtain 119 g (white powder; yield: 84.5%) of the intermediate (28). Results of NMR measurement of the thus-obtained intermediate (28) are as follows. 1H-NMR (300 MHz, d-DMSO) 7.80 (s, 1H), 7.52 (s, 2H), 5.98 (s, 1H), 4.13 (s, 4H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1193-21-1, 4,6-Dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; FUJIFILM Corporation; EP2253672; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 945950-37-8, 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 945950-37-8, name is 4-Methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Suspended in 30mL of DCM was 4-methyl -7H- pyrrolo [2,3-d] pyrimidine (1g, 7.51mmol) was added N- iodosuccinimide (1.86g, 8.26mmol).It was stirred at room temperature for 2 hours the reaction mixture.The volatiles were removed in vacuo.Of anhydrous ethyl acetate and 50% saturated NaHCO3The residue obtained was extracted.With water and the organic layer was washed with brine, dried (MgSO4), Filtered and the volatiles removed in vacuo.The residue was suspended in acetonitrile and sonicated for 45 minutes.The solid was collected by filtration to give 5-iodo-4-methyl–7H- pyrrolo [2,3-d] pyrimidine (1.69 g).

According to the analysis of related databases, 945950-37-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pulaixike Company; Zhang, Chao; Ibrahim, Prabha N; Nespi, Marika; Shi, Songyuan; Spevak, Wayne; Habets, Gaston G; Burton, Elizabeth A; Hirth, Klaus-Peter; (181 pag.)CN105228983; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4359-87-9 ,Some common heterocyclic compound, 4359-87-9, molecular formula is C4Cl3N3O2, 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 suspension of 2,4,6-trichloro-5-nitropyrimidine (0.8g, 3.5mmol) inTHF (30ml) was added [l-(4-Amino-phenyl)-cyclobutyl]-carbamic acid tert-butyl ester (0.827g, 3.15mmol) at 15C. The mixture was stirred for 30min at 15C. The reaction mixture was concentrated and was purified by flushing chromatography on silica gel (eluting with Hexane EtOAc=100/l~3/l) to give tert-butyl l-(4-(2,6-dichloro-5-nitropyrimidin-4- ylamino)phenyl)cyclobutylcarbamateas a yellow solid (0.45g, 31.5% yield). ‘HNMR (CDCI3, 400 MHz): S9AS(s, 1H), 7.49 (s, 4H), 5.12 (s, ??,), 2.55-2.51(m, 4?), 2.13-2.04(m, 1H),1.89-I.86(m, lH),1.42(s, 9H); LC/MS: (ESI+) e/z: 454.3 [M+l]+, 456.3 [M+3]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4359-87-9, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5751-20-2, 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.5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one, molecular formula is C5H6N2OS, molecular weight is 142.18, as common compound, the synthetic route is as follows.

Example 11 Synthetic route

The chemical industry reduces the impact on the environment during synthesis 5751-20-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Changyou; ZOU, Wuxin; HUA, Yuxia; DANG, Qun; WO2011/133444; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-61-4, Adding some certain compound to certain chemical reactions, such as: 22536-61-4, name is 2-Chloro-5-methylpyrimidine,molecular formula is C5H5ClN2, 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 22536-61-4.

2-Chloro-5-methyl-pyrimidine (18 mL, 151 mmol), potassium (Z)-but-2-en-2- yltrifluoroborate (Sigma Aldrich, 31 g, 191 mmol), tricyclohexyiphosphine (8.5 g, 30.2 mmol), and Pd2(dba)3 (13.82 g, 15.09 mmol) were added to a flask which was then degassed and backfilled with nitrogen. To the flask was added 1 ,4-dioxane (252 mL) and aqueous potassium phosphate tribasic (37.5 mL, 453 mmol). The resulting reaction was heated at 100C for 16 h. The reaction was then cooled to RT. The residue was filtered through a plug of silica gel and then loaded onto silica gel (0-20% EtOAc in heptanes) to afford (E)-2-(but-2-en-2-yl)-5-methylpyrimidine, Example 371.01 (19 g, 125 mmol), in 83% yield.

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. 22536-61-4, 2-Chloro-5-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3435-28-7, 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. 3435-28-7, name is 6-Methylpyrimidin-4-amine, molecular formula is C5H7N3, 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.

a) 2-Chloro-N-(6-methyl-pyrimidin-4-yl)-acetamide 6-Methyl-pyrimidin-4-yl amine (545 mg) was suspended in DCE (5 mL) and chloroacetylchloride (0.4 mL) was added dropwise. The reaction was heated in a microwave at 80 C. for 5 mins. The reaction mixture was cooled, filtered and a solid obtained.

According to the analysis of related databases, 3435-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bull, Richard James; Skidmore, Elizabeth Anne; Ford, Rhonan Lee; Mather, Andrew Nigel; Mete, Antonio; US2011/172237; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia