Category: pyrimidines

Adding a certain compound to certain chemical reactions, such as: 52522-99-3, 5-Iodo-2,4-dimethoxypyrimidine, 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, Product Details of 52522-99-3, blongs to pyrimidines compound. Product Details of 52522-99-3

Preparation 70: 5-(2-Chloro-5-fluoro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep70); 5-lodo-2,4-dimethoxy-pyrimidine (868 mg, 3.3 mmol) was dissolved in degassed n-PrOH (30 ml) and then 2-chloro-5-fluoropyridine-3-boronic acid (858 mg, 4.9 mmol), Na2CO3 (700 mg, 6.6 mmol), PPh3 (88 mg, 0.33 mmol) and Pd(OAc)2 (90 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between brine and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether 2-8 affording 240 mg of the title compound (27% yield). MS (ES) (m/z): 270 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52522-99-3, 5-Iodo-2,4-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Glaxo Group Limited; WO2007/113232; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3435-25-4, Adding some certain compound to certain chemical reactions, such as: 3435-25-4, name is 4-Chloro-6-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 3435-25-4.

A solution of 6-methoxy-7-(2-(methylamino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (363 mg, 1 mmol) and 4-chloro-6-methylpyrimidine (257 mg, 2 mmol), (J. Het. Chem., 1969, 6, 879), in N,N-diisopropylethylamine (2 ml) was heated at reflux for 30 minutes. The volatiles were removed by evaporation and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluding with methylene chloride/methanol (95/5) to give 6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (365 mg, 80%). 1 H NMR Spectrum: (CDCl3) 1.19(s, 9H); 2.36(s, 3H); 3.18(s, 3H); 3.95(s, 3H); 4.09(t, 2H); 4.34(t, 2H); 5.9(s, 2H); 6.3(s, 1H); 7.14(s, 1H); 7.63(s, 1H); 8.17(s, 1H); 8.5(s, 1H) MS-ESI: 456 [MH]+

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. 3435-25-4, 4-Chloro-6-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 695-85-2, 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.695-85-2, name is 4-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.56, as common compound, the synthetic route is as follows.

1-(t-Butoxycarbonyl)-4-(5-methoxy-4-pyrimidyl)-3-methylpiperazine A mixture of 1-(t-butoxycarbonyl)-3-methylpiperazine (2.0 g, 0.01 mole), 4-chloro-5-methoxypyrimidine (1.5 g, 0.01 mole) and diisopropylethylamine (2.6 mL, 0.015 mole) in 25 mL of dry acetonitrile was heated to reflux under Ar for 60 h. The resulting solution was diluted with ether and then washed (H2O, brine), dried (Na2SO4) and evaporated to give a gum. This gum was triturated with hexane ( 3) and the supernatant was evaporated to give a gum. Flash chromatography (SiO2/ethyl acetate-hexane=1:1, then ethyl acetate) of this material gave first 4-chloro-5-methoxypyrimidine (0.4 g, 27%) and then the desired product (1.2 g, 30%) as a light pink solid: m.p. 70-72 C.; IR (KBr) 1690, 1575 cm-1; 1H nmr (200 MHz, CDCl3) delta8.33 (s, 1H), 7.90 (s, 1H), 4.79 (br s, 1H), 4.4-3.8 (m, 3H), 3.86 (s, 3H), 3.35-2.90 (m, 3H), 1.48 (s, 9H), 1.21 (d, J=6.7 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis 695-85-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Fabre-Kramer Pharmaceuticals, Inc.; US2009/281114; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. Computed Properties of C5H4Cl2N2S

Prepared by methods substantially similar to those set forth in Koppell et al, JOC, 26,1961, 792, in the following manner. To a stirred solution of 4, 6-dichloro-2- (methylthio) pyrimidine (50 g, 0.26 mol) in dichloromethane [(1] L) at [0C] was added meta-chloroperoxybenzoic acid (143.6 g, 0.64 mol) over a period of 20 minutes. The solution was allowed to warm to room temperature and was stirred for 4 hours. The mixture was diluted with dichloromethane (1.5 L) and then treated sequentially with 50% [NA2S203/NAHC03] solution (2 x 200 ml), sat. [NAHC03] solution (4 x 300 ml), and brine (200 ml) then dried [(MGS04).] The solvent was removed in vacuo to afford an off-white solid which was redissolved in EtOAc [(1 L)] and treated sequentially with sat. [NAHC03] solution (3 x [300] ml), and brine (100 [ML)] then dried (MgS04). The solvent was removed in vacuo to afford the title compound (A) as a white solid (55.6 g, 96% yields NMR [CDC13] [5] 3.40 (3H, s, CH3), 7.75 [(1H.] s. ArH).

The synthetic route of 6299-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2004/833; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 695-85-2, 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. 695-85-2, name is 4-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, 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.

1-(t-Butoxycarbonyl)-4-(5-methoxy-4-pyrimidyl)-3-methylpiperazine A mixture of 1-(t-butoxycarbonyl)-3-methylpiperazine (2.0 g, 0.01 mole), 4-chloro-5-methoxypyrimidine (1.5 g, 0.01 mole) and diisopropylethylamine (2.6 mL, 0.015 mole) in 25 mL of dry acetonitrile was heated to reflux under Ar for 60 h. The resulting solution was diluted with ether and then washed (H2 O, brine), dried (Na2 SO4) and evaporated to give a gum. This gum was triturated with hexane (x3) and the supernatant was evaporated to give a gum. Flash chromatography (SiO2 /ethyl acetate-hexane=1:1, then ethyl acetate) of this material gave first 4-chloro-5-methoxypyrimidine (0.4 g, 27%) and then the desired product (1.2 g, 30%) as a light pink solid: m.p. 70-72 C.; IR (KBr) 1690, 1575 cm-1; 1 H nmr (200 MHz, CDCl3) delta 8.33 (s, 1H), 7.90 (s, 1H), 4.79 (br s, 1H), 4.4-3.8 (m, 3H), 3.86 (s, 3H), 3.35-2.90 (m, 3H), 1.48 (s, 9H), 1.21 (d, J=6.7 Hz, 3H).

According to the analysis of related databases, 695-85-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US5434154; (1995); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 956034-07-4, 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.956034-07-4, name is 2,4-Dichlorofuro[3,2-d]pyrimidine, molecular formula is C6H2Cl2N2O, molecular weight is 188.9989, as common compound, the synthetic route is as follows.

Under nitrogen, to a suspension of compound 5-a (640 mg, 1.65 mmol), compound 30-c (280 mg, 1.49 mmol) and potassium carbonate (720 mg, 5.2 mmol) in 1,4-dioxane (2 mL) and water (6 mL) was added Pd(PPh3)4 (57 mg, 0.05 mmol), the mixture was heated to 80 C. and stirred for 16 hours. The mixture was then concentrated under reduced pressure, the residue was diluted with water (20 mL), extracted with dichloromethane (20 mL×3). The organic layer were combined, washed with water (10 mL×3) and saturated brine (10 mL) in sequence, then dried over anhydrous sodium sulfate, filtrated, the filtrate was concentrated under reduced pressure. The residue was purified by silica column chromatography (petroleum ether:ethyl acetate=3:1) to give light yellow solid 30-b (620 mg, yield: 70%). LC-MS (ESI): nm/z=415 [M+H]+.

Statistics shows that 956034-07-4 is playing an increasingly important role. we look forward to future research findings about 2,4-Dichlorofuro[3,2-d]pyrimidine.

Reference:
Patent; SHANGHAI CHEMEXPLORER CO., LTD.; XU, Zusheng; ZHANG, Nong; SUN, Qingrui; WANG, Tinghan; US2015/336982; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)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, SDS of cas: 153435-63-3, blongs to pyrimidines compound. SDS of cas: 153435-63-3

(S)-(5-(((5-chloropyridin-2-yl)amino)methyl)-6-azaspiro[2.5]octan-6-yl)(5-fluoro-2-(pyrimidin-2-yl)phenyl)methanone Intermediates 4 (1 eq) was dissolved dry DMF (20 ml/mmol), then CsF (2 eq), CuI (0.2 eq), [Ph3P]4Pd (0.1 eq) and 2-(tributylstannyl)pyrimidine (1.5 eq; prepared according to Eur. J. Org. Chem. 2003, 1711-1721) was added. The mixture was warmed at 130 C. for 10 minutes (microwave), then poured in aqueous saturated solution of NH4Cl and extracted with AcOEt. The organic layers were combined, dried (Na2SO4) and concentrated under vacuum; crude product was purified by silica gel column chromatography (DCM to DCM/MeOH 9/1) to obtain the title compound with yield of 15%. 1HNMR (CDCl3) delta ppm 8.80-8.93 (m, 1H), 8.64 (d, 1H), 8.24-8.50 (m, 1H), 7.83-8.08 (m, 1H), 6.89-7.40 (m, 4H), 6.17-6.56 (m, 1H), 5.11-5.25 (m, 1H), 4.3-4.9 (m, 1H), 3.6-4.0 (m, 2H), 3.01-3.47 (m, 2H), 1.92-2.38 (m, 1H), 1.45-1.8 (m, 1H), 0.65-1.12 (m, 1H), 0.17-0.59 (m, 4H). ESI+m/z 474 [M+Na]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ROTTAPHARM S.P.A.; Stasi, Luigi Piero; Rovati, Lucio; US2013/310400; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1224288-95-2 ,Some common heterocyclic compound, 1224288-95-2, molecular formula is C7H4N4O, 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 mixture of 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (1.33 g, 8.31 mmol) and POCl3 (7.74 mL, 83 mmol) was heated at 150 C. for 3 hours and cooled to room temperature. After concentration in vacuo, the residue was purified by column chromatography on SiO2 (Hex:EtOAc=2:1) to afford 5-chloropyrazolo[1,5-a]pyrimidine-3-carbonitrile (343 mg, 23%) as a white solid. 1H-NMR (CDCl3, Varian, 400 MHz): delta 7.09 (1H, d, J=7.6 Hz), 8.39 (1H, s), 8.68 (1H, d, J=7.2 Hz).

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. 1224288-95-2, 5-Oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HANDOK INC.; CMG Pharmaceutical Co., Ltd.; Kim, Moonsoo; Lee, Chaewoon; Lee, Gilnam; Yoon, Cheolhwan; Seo, Jeongbeob; Kim, Jay Hak; Lee, Minwoo; Jeong, Hankyul; Choi, Hyang; Jung, Myung Eun; Lee, Ki Nam; Kim, Hyun Jung; Kim, Hye Kyoung; Lee, Jae Il; Lee, MinWoo; Kim, Misoon; Choi, Soongyu; (124 pag.)US2016/168156; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 6153-44-2, 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. 6153-44-2, name is Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Methyl 2,6-dioxo-l,2,3,6-tetrahydropyrimidine-4-carboxylate (5 g, 29.4 mmol) and DMF (118 mL) were combined and the resultant mixture was cooled with an ice bath. Lithium hydride (0.369 g, 44.1 mmol) was added in portions. The mixture was stirred for 20 minutes and ((chloromethoxy)methyl)benzene (5.00 mL, 32.3 mmol) was added via syringe. The mixture was stirred a 00C for 30 minutes. Lithium hydride (0.492 g, 58.8 mmol) was then added in portions and stirred for 10 minutes. 2-(Bromomethyl)pyridine hydrobromide (8.92 g, 35.3 mmol) was added in portions and stirred at 00C over 1 hour. The bath was removed and then stirred at room temperature for 2 hours. Water (25 mL) and methanol (25 mL) were added and the solvents were evaporated under vacuum at 65°C to leave a red oily solid, which was partitioned between IN NaOH (100 mL) and diethyl ether (50 mL). The organic layer was separated. The aqueous layer was washed with diethyl ether (2 x 50 mL) and the aqueous layer was acidified to pH=4 with 3N HCl. The aqueous layer was washed with diethyl ether (2 x 50 mL). The aqueous layer was then extracted with n-BuOH (4 x 100 mL). The organic layers from the n-BuOH extraction were combined and the solvent was evaporated under vacuum to give a solid, which was triturated with acetone and cooled in an ice bath. The resulting solid was isolated by filtration and dried under vacuum to give 4.86 g of a first crop of the title compound; a second and third crop were isolated to give a total of 5.53g of the title compound. MS [M+H] found 368.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6153-44-2, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FENG, Jun; KEUNG, Walter; LARDY, Matthew; WO2010/129848; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 56686-16-9 ,Some common heterocyclic compound, 56686-16-9, molecular formula is C6H7BrN2O2, 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.

5-Formyl-2,4-dimethoxypyrimidine A solution of 1.6M n-Buli in hexane (48 ml, 73.6 mmol) was added over 5 min. to a stirred suspension of 5-bromo-2,4-dimethoxypyrimidine (16 g; 72.9 mmol) in dry Et2 O (240 ml) at -70 C. under an atmosphere of dry N2. Dry ethyl formate (28 g: 377 mmol) was added and the orange solution stirred at -70 C. for 1 h then allowed to warm slowly to ambient temperature. Water (400 ml) was added and the aqueous layer separated and extracted with Et2 O (3*200 ml). The ether layer was combined with the extracts and dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography by preloading in SiO2 and eluding with EtOAc-hexane (3:7, v/v). Product fractions were combined and evaporated to give fine white needles, yield 6.89 g, (56%). Mass spectrum m/z 169 (M+H)+ Analysis, found: C, 50:1;H,4.5;N,16.9%;C7 H8 N2 O3 requires C,50.00; H,4.79; N, 16.66%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56686-16-9, its application will become more common.

Reference:
Patent; University of Birmingham; US5356882; (1994); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia