Category: pyrimidines

Synthetic Route of 926304-76-9, 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 926304-76-9 as follows.

To a solution of the above pyrimidine (428 mg, 1.38 mmol), bis(triphenylphosphine)palladium(II) dichloride (145 mg, 0.207 mmol) and LiCl (289 mg, 6.9 mmol) in degassed DMF (5 mL) was added tributyl(vinyl)tin (0.48 mL, 1.64 mmol) and the mixture was heated at 1000C overnight. Standard work-up and purification afforded 4-(5- vinyl-pyrimidin-2-yloxy)-benzoic acid methyl ester (210 mg, 59%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,926304-76-9, its application will become more common.

Reference:
Patent; ANORMED INC.; WO2007/22371; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 99420-75-4, 5-Methylpyrimidine-2-carboxylic acid, 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 5-Methylpyrimidine-2-carboxylic acid, blongs to pyrimidines compound. Safety of 5-Methylpyrimidine-2-carboxylic acid

To a solution of methanol (50 mL) was added SOCl2 (5.17 g, 43.5 mmol, 3.00 equiv) dropwise at 0 C. The resulting solution was stirred for 0.5 h at 25 C. This was followed by the addition of 5-methylpyrimidine-2-carboxylic acid [Example 9, Step 1] (2 g, 14.5 mmol, 1.00 equiv). The resulting solution was stirred for 1 h at 65 C. The resulting mixture was concentrated under vacuum to remove methanol and SOCl2. The resulting solution was diluted with H2O (30 mL). The resulting solution was extracted with ethyl acetate (3×30 mL). The organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 2 g (90.7%) of methyl 5-methylpyrimidine-2-carboxylate as a yellow solid. LC-MS: m/z=153 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,99420-75-4, 5-Methylpyrimidine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; ZHANG, Chengzhi; (94 pag.)US2018/79742; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 220041-42-9, 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. 220041-42-9, name is tert-Butyl 2-chloropyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

In a 20 mE vial under nitrogen, tert-butyl 2-chloropyrimi- dine-4-carboxylate (0.200 g, 0.932 mmol), 4-methylpiperi- din-3-ol hydrochloride (0.185 g, 1.220 mmol) and triethylamine (0.52 mE, 3.73 mmol) were added to THF (14 mE) and the resulting mixture was stirred at 80 C. for 16 h. The cooled mixture was concentrated in vacuo and the residuewas purified on the ISCO using a 25 g Innoflash column (Hexane/EtOAc) to give tert-butyl 2-(3-hydroxy-4-methyl-piperidin-1-yl)pyrimidine-4-carboxylate (0.269 g, 98%) as ayellow oil which was a mixture of diastereomers. EC (Analytical MethodA): 2.081 mi ECMS (APCI): calcd forC,5H24N303 [M+H] mlz 294.18; found 294.2. ?H NMR (400 MHz, CDC13) 0 8.45 (d, J=4.7 Hz, 1H), 7.02 (d, J=4.7Hz, 1H), 4.87 (ddd, J=1.6, 4.5, 12.7 Hz, 1H), 4.74-4.63 (m, 1H), 3.30 (tt, J=4.8, 9.4 Hz, 1H), 2.98 (ddd, J=2.7, 12.1, 13.3Hz, 1H), 2.84 (dd, J=10.0, 12.7 Hz, 1H), 1.87-1.74 (m, 1H),1.70 (d, J=4.7 Hz, 1H), 1.66-1.57 (m, 1H), 1.61 (s, 9H),1.36-1.20 (m, 1H), 1.10 (d, J=6.7 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,220041-42-9, its application will become more common.

Reference:
Patent; UNIVERSITE DE MONTREAL; Martel, Alain; Tremblay, Francois; (65 pag.)US9598419; (2017); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 89792-07-4, 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 89792-07-4, name is 2-Methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

An equal volume of dichloromethane (50 ml) and tetrahydrofuran (50 ml) were mixed,The compound 2-methyl-7H- [2,3-d] pyrrolopyrimidine (10 mmol) was added to the system,After stirring for 20 minutes,System cooling to 0-5 ,JoinTribromopyridinium(20 mmol),The system continues at 0-5 CStirring for 1 hour,The reaction mixture was slowly added to an aqueous solution of saturated sodium carbonate. The system was stirred at 20 C overnight and under reduced pressure Filtered, washed with water, dried at 55 C,To give 1.8 g of a yellow solid 4-bromo-2-methyl-7H- [2,3-d] pyrrolopyrimidine in 85% yield.

According to the analysis of related databases, 89792-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu Shuangwei; (11 pag.)CN106967073; (2017); A;,
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 1321618-96-5, name is 4-Chloro-5-methylfuro[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-Chloro-5-methylfuro[2,3-d]pyrimidine

To a solution of 4-chloro-5-methylfuro[2,3-d]pyrimidine (12, 85 mg, 0.5 mmol) and 4-methoxy-N-methylaniline (5, 80 mg, 5.75 mmol) in 2 mL of anhydrous isopropanol (IPA) added 2 drops of concentrated HC1 and the reaction mixture was stirred at room temperature overnight. The brown precipitate was collected by filtration, washed with cold isopropanol, and dried under vacuum to afford compound 2 (95 mg, 75 %) as brown solid. Analytical data of compound 2 is identical with the product obtained using previous method.12

With the rapid development of chemical substances, we look forward to future research findings about 1321618-96-5.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; KUMAR, Dileep; MANN, J., John; (109 pag.)WO2019/89575; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 114040-06-1, 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. 114040-06-1, name is 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 3-bromo-5,7-dichloropyrazolo[l,5-a]pyrimidine (14.6 g, 55.3 mmol) in DCM (200 mL) was added cis-hydroxy-3- methylcyclobutane-l-methylamine (7.0 g, 60.9 mmol), and DIPEA (19.2 mL, 110.6 mmol). The reaction was stirred at rt for 16 h. Water and DCM were added to separate the phases and the aqueous phase was extracted with DCM. The combined organic extracts were dried over Na2S04, filtered and concentrated to give the title compound as a yellow solid (18.1 g, 95%). H NMR (400 MHz, CDCk) delta ppm 7.96 (s, 1 H), 6.60-6.49 (m, 1H), 5.99 (s, 1H), 3.47 (t, J = 6.0 Hz, 2H), 2.38-2.27 (m, 3H), 1.96-1.85 (m, 2H), 1.43 (s, 3H); MS ESI [M + H]+ 345.1, calcd for [Ci2Hi4BrClN40 + H]+ 345.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,114040-06-1, 3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LAUFER, Radoslaw; NG, Grace; LI, Sze-Wan; PAULS, Heinz W.; LIU, Yong; PATEL, Narendra Kumar B.; WO2015/70349; (2015); 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. 38275-61-5, name is 5-Chloropyrimidine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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. HPLC of Formula: C5H3ClN2O2

Toa solution of 5-chloropyrimidine-2-carboxylic acid (0.16 g, 1.0 mmol) and (3S,3aS) -3- (aminomethyl) -7- (3-oxomorpholino) -3a, 4-dihydrobenzo [b] oxazolo[3, 4-d] [1, 4] oxazin-1 (3H) -one (0.32 g, 1.0 mmol) in N, N-dimethylformamide(10 mL) were added 1- (3-dimethylaminopropyl) -3-ethylcarbodiimidehydrochloride (0.38 g, 2.0 mmol) and 4-dimethylaminopyridine (0.31 g, 2.5 mmol). The mixture was reacted at rt for 10 hours. The reaction mixture wasconcentrated in vacuo to remove the solvent, and to the residue was addeddichloromethane (30 mL) . The resulting mixture was washed with aqueous sodiumhydroxide (10 mL, 2.0 mol/L) and water (10 mL) in turn, dried over anhydroussodium sulfate and filtered. The filtrate was concentrated in vacuo to remove thesolvent, and the crude product was purified by silica gel chromatography elutedwith DCM/MeOH (V/V) 30/1 to give the title compound as a white solid (0.167g, 36) . The compound was characterized by the following spectroscopic data:MS (ESI, pos. ion) m/z: 460.20 (M+1) and 1H NMR (400 MHz, d6-DMSO): delta 9.28 (t, J 6.0 Hz, 1H) , 9.10 (s, 2H) , 7.85 (d, J 8.7 Hz, 1H) , 7.05(d, J 2.2 Hz, 1H) , 7.01 (dd, J 8.7, 2.3 Hz, 1H) , 4.65 (dd, J 12.3, 5.6Hz, 1H) , 4.54 (dd, J 10.3, 3.0 Hz, 1H) , 4.17 (s, 2H) , 4.15 -4.01 (m, 2H) ,3.98 -3.92 (m, 2H) , 3.84 -3.74 (m, 2H) , 3.72 -3.65 (m, 2H) .

With the rapid development of chemical substances, we look forward to future research findings about 38275-61-5.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Jiancun; ZUO, Yinglin; ZHANG, Yingjun; WANG, Xiaojun; ZHANG, Jin; WEN, Liang; CHENG, Guanjun; WO2015/110024; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1060815-90-8, 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. 1060815-90-8, name is 2-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

A.21 (400 mg, 1.43 mmol), benzenesulphonyl chloride (272 muL, 2.13 mmol), DMAP (18 mg, 0.15 mmol) and Hnig base (350 muL, 2.17 mmol) are taken up in 10 mL DCM and stirred for 16 h at 200C. The solvent is eliminated in vacuo, the residue is purified by column chromatography (method prep. HPLC2; 10 % acetonitrile to 95 % in 12 min) and A.21-PG (HPLC-MS: tRet. = 1.98 min; MS(M+H)+ = 420; method FEC3) is obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1060815-90-8, 2-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; BOEHMELT, Guido; KOFINK, Christiane; KUHN, Daniel; MCCONNELL, Darryl; STADTMUELLER, Heinz; WO2010/7116; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 60331-15-9, Adding some certain compound to certain chemical reactions, such as: 60331-15-9, name is 4-Chloro-6-methoxy-2-methyl-5-nitropyrimidine,molecular formula is C6H6ClN3O3, 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 60331-15-9.

EXAMPLE 4 3-(6-Methoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine A solution of 0.204 g (1.0 mmol) of 2-methyl-4-methoxy-5-nitro-6-chloro-pyrimidine [Helv. (1958), 41, 1806], 0.20 g (1.1 mmol) 2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride [J. Heterocycl. Chem. (1971), 8(5), 779-83] and 0.30 g (3.0 mmol) triethylamine in 10.0 ml N,N-dimethylformamide was stirred at room temperature for 60 h. The reaction mixture was then poured into 50 ml of an ice/water mixture and extracted three times with 60 ml of dichloromethane. The combined organic phases were washed twice with 50 ml of water, dried over magnesium sulphate, evaporated under reduced pressure and dried in a high vacuum. The residue obtained was then crystallized from dichloromethane/hexane to yield 0.28 g (0.9 mmol), 90%,3-(6-methoxy-2-methyl-5-nitro-pyrimidin-4-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow solid; m.p. 123-128 C.

According to the analysis of related databases, 60331-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US6218385; (2001); B1;,
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. 14631-08-4, name is 2-Chloropyrimidine-4,5-diamine. A new synthetic method of this compound is introduced below., Safety of 2-Chloropyrimidine-4,5-diamine

Intermediate 82: Mixture /V-(5-amino-2-chloro-4-pyrimidinyl)-2-oxo-3-phenyl-1-oxa-3- azaspiro[4.51decane-8-carboxamide and lambda/-(4-amino-2-chloro-5-pyrimidinyl)-2-oxo-3- phenyl-1-oxa-3-azaspiro[4.51decane-8-carboxamide; (Trans^-oxo-S-phenyl-i-oxa-S-azaspiro^.deltaJdecane-delta-carboxylic acid (Intermediate 10 alternative preparation, 239 mg, 0.286 mmol), 2-chloro-4,5-pyrimidinediamine (commercially available, 41.4 mg, 0.286 mmol) and EDC HCI (88 mg, 0.458 mmol) were dissolved in pyridine (2 ml) and stirred at room temperature overnight. The solvent was removed under vacuum to give a residue which was purified by silica gel chromatography (5g cartridge) eluting in gradient with CyclohexaneEtOAc 9:1 to 1 :1 then DCMMeOH 95:5 to afford the title compound as a pale yellow solid (35 mg, 30%), mixture of regio and stereoisomers with unknown ratio). UPLC-MS: 0.60 min, m/z 402 [M+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, 14631-08-4, 2-Chloropyrimidine-4,5-diamine.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia