Category: pyrimidines

Adding a certain compound to certain chemical reactions, such as: 871254-61-4, 2,4-Dichloropyrimidine-5-carbaldehyde, 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: 871254-61-4, blongs to pyrimidines compound. Recommanded Product: 871254-61-4

The mixture of 9 (8.8 g, 50.0 mmol) and Et3N (15.2 g, 150.0 mmol)in THF (150 mL) was stirred at 0 C for 10 min under argon. To the solution was added 3-nitrobenzylhydrazine dihydrochloride (11.2 g,55.0 mmol) and then warm to r.t. and stirred for 4 h. The solvent wasremoved in vacuo, and the residue was partitioned between CH2Cl2(50 mL) and H2O (100 mL). The layers were separated, and the aqueouslayer was extracted with CH2Cl2 (2 × 50 mL). The combined organiclayers were dried over anhydrous sodium sulfate, filtered, and concentratedto provide the crude product, which was purified by silica gelcolumn chromatography (eluting with 0-10% MeOH in DCM) to provide10a, white solid, yield 62% (9.0 g, 31.1 mmol). 1H NMR(300 MHz, CDCl3) delta 8.93 (s, 1H), 8.25 (m, 1H), 8.18 (m, 1H), 8.07 (s,1H), 7.71 (d, J = 9 Hz, 1H), 7.53 (t, J = 9 Hz, 1H), 5.71 (s, 2H); MS(ESI) m/z: 290.1 [M+H]+.

The synthetic route of 871254-61-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yin, Yuan; Chen, Cheng-Juan; Yu, Ru-Nan; Shu, Lei; Wang, Zhi-Jian; Zhang, Tian-Tai; Zhang, Da-Yong; Bioorganic Chemistry; vol. 98; (2020);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 302964-08-5, 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.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, molecular weight is 394.2783, as common compound, the synthetic route is as follows.

Compound I is prepared according to the procedure described in US/2006/0004067A1 (Bang-Chi Chen, et al, published Jan. 05, 2006).

Statistics shows that 302964-08-5 is playing an increasingly important role. we look forward to future research findings about 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/219370; (2007); A1;,
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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.1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, molecular formula is C14H17ClN4O, molecular weight is 292.76, as common compound, the synthetic route is as follows.SDS of cas: 1211443-61-6

2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-6-carboxamide (500 mg, 1.71 mmol) was suspended in 20 mL of 1,4 – in dioxane,2-Amino-5-nitropyridine (356 mg, 2.56 mmol), Pd(OAc) 2 (9.6 mg, 0.043 mmol),BINAP (53 mg, 0.09 mmol) and Cs2CO3 (834 mg, 2.56 mmol) were applied to argon for 3 times and warmed to 100 C overnight.After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.The crude silica gel column was chromatographed to give 200 mg of desired product 3-7.Yellow solid with a yield of 30%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211443-61-6, 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; Nankai University; Xiang Rong; Fan Yan; Li Yongtao; Guo Qingxiang; Huang Zhi; Wang Xin; Zhang Chao; Liu Yanhua; (32 pag.)CN108929324; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
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Synthetic Route of 1195768-23-0, 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. 1195768-23-0, name is N-(3-(2-(tert-Butyl)-5-(2-chloropyrimidin-4-yl)thiazol-4-yl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide. A new synthetic method of this compound is introduced below.

Step D : N- { 3 – [ 5-(2-amino-4-pyrimidiny l)-2-( 1 , 1 -dimethy lethyl)- 1 ,3 -thiazol-4-yl] -2- fluorophenyl} -2,6-difluorobenzenesulfonamide: In 1 gal pressure reactor, a mixture of N- {3-[5-(2-chloro-4-pyrimidinyl)-2-(l,l- dimethylethyl)-l,3-thiazol-4-yl]-2-fluorophenyl} -2,6-difluorobenzenesulfonamide (120 g) prepared in accordance with Step C, above, and ammonium hydroxide (28-30%, 2.4 L, 20 vol) was heated in the sealed pressure reactor to 98-103 C and stirred at this temperature for 2 hours. The reaction was cooled slowly to room temperature (20 C) and stirred overnight. The solids were filtered and washed with minimum amount of the mother liquor and dried under vacuum. The solids were added to a mixture of EtOAc (15 vol)/ water (2 vol) and heated to complete dissolution at 60-70 C and the aqueous layer was removed and discarded. The EtOAC layer was charged with water (1 vol) and neutralized with aq. HC1 to ~pH 5.4-5.5. and added water (lvol). The aqueous layer was removed and discarded at 60-70 C. The organic layer was washed with water (1 vol) at 60-70 C and the aqueous layer was removed and discarded. The organic layer was filtered at 60 C and concentrated to 3 volumes. EtOAc (6 vol) was charged into the mixture and heated and stirred at 72 C for 10 min , then cooled to 20C and stirred overnight. EtOAc was removed via vacuum distillation to concentrate the reaction mixture to ~3 volumes. The reaction mixture was maintained at ~65-70C for ~30mins. Product crystals having the same crystal form as those prepared in Example 58b (and preparable by the procedure of Example 58b), above, in heptanes slurry were charged. Heptane (9 vol) was slowly added at 65-70 C. The slurry was stirred at 65-70 C for 2-3 hours and then cooled slowly to 0-5C. The product was filtered, washed with EtO Ac/heptane (3/1 v/v, 4 vol) and dried at 45 C under vacuum to obtain N- {3 – [5 -(2-amino-4-pyrimidinyl)-2-( 1 , 1 -dimethylethyl)- 1 , 3 -thiazol-4-yl] -2- fluorophenyl}-2,6-difluorobenzenesulfonamide (102.3 g, 88%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1195768-23-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; CAPONIGRO, Giordano; HORN-SPIROHN, Thomas; LEHAR, Joseph; (49 pag.)WO2017/37587; (2017); A1;,
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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. 1152107-25-9, name is Gsk-1322322. A new synthetic method of this compound is introduced below., Recommanded Product: Gsk-1322322

Example 8 [(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-6-[(9aS)-hexahydropyrazino [2,1 -c] [1 ,4] oxazin- 8(1 H)-yl]-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl] hydroxyl formamide dimethanesulphonate. Crystalline [(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-6-[(9aS)- hexahydropyrazino[2, 1 -c][1 ,4]oxazin-8(1 H)-yl]-2-methyl-4-pyrimidinyl}hydrazino)-3- oxopropyl]hydroxyformamide (100 mg) was dissolved in ethyl acetate (10 ml_). Methanesulphonic acid (40.1 mg) in ethyl acetate (ca. 10 ml.) was prepared. The methanesulphonic acid solution was added dropwise to the solution of freebase in ethyl acetate. A precipitate was formed. The slurry was stirred and aged overnight. The precipitate’s crystallinity was verified by polarized light microscopy. The precipitate and supernatant were separated by filtration. The solids were then vacuum dried. The resulting solid was analytically characterized and found to be Form 1 of the dimethanesulphonate salt of [(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-6-[(9aS)- hexahydropyrazino[2, 1 -c][1 ,4]oxazin-8(1 H)-yl]-2-methyl-4-pyrimidinyl}hydrazino)-3- oxopropyl]hydroxyformamide by XRPD (see Figure 7). X-Rav Powder Diffraction of r(2R)-2-(Cvclopentylmethyl)-3-(2-f5-fluoro-6-r(9aS)- hexahvdropyrazinor2,1-ciri,41oxazin-8(1 H)-vn-2-methyl-4-pyrimidinyl>hvdrazino)-3- oxopropyUhydroxyformamide dimethanesulphonate The XRPD pattern for polymorphic Form 1 of [(2R)-2-(Cyclopentylmethyl)-3-(2-{5- fluoro-6-[(9aS)-hexahydropyrazino[2, 1 -c][1 ,4]oxazin-8(1 H)-yl]-2-methyl-4- pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide dimethanesulphonate is presented in Figure 7. The X-ray powder diffractogram was collected with a diffraction system utilizing copper Ka radiation, automated divergent slits, nickel Kappabeta filter, and multiple strip detector. Sample presentation consisted of a thin powder layer mounted on a silicon zero background wafer. Thermal Analysis Based on differential scanning calorimetry (DSC) seen in Figure 8 and thermogravimetric analysis (TGA) seen in Figure 9, polymorphic Form 1 of [(2R)-2- (cyclopentylmethyl)-3-(2-{5-fluoro-6-[(9aS)-hexahydropyrazino[2,1 -c][1 ,4]oxazin-8(1 h)-yl]- 2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide dimethanesulphonate decomposes at ca. 180 to 185 C under nitrogen.

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, 1152107-25-9, Gsk-1322322.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO. 2) LIMITED; AUBART, Kelly, Marshall; GILLIAN, Jason, Michael; QIN, Donghui; MCKEOWN, Robert, Rahn; WILLIAMS, Glenn, R.; WO2013/82388; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 696-07-1, Adding some certain compound to certain chemical reactions, such as: 696-07-1, name is 5-Iodouracil,molecular formula is C4H3IN2O2, 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 696-07-1.

General procedure: To a solution of 5-iodopyrimidine (0.84 mmol) in anhydrous DMF (7 mL) were added the terminal alkyne (2.5 mmol), Pd(PPh3)4 (0.08 mmol), CuI (0.08 mmol) and Et3N [or (iPr)2EtN] (1.68 mmol). Method A: The reaction mixture was stirred at room temperature overnight. The extent of the reaction was monitored by TLC and the solvent was evaporated in vacuo and the residue purified by column chromatography (initial eluent CH2Cl2, then CH2Cl2/MeOH = 40:1) to afford 1-10a and 1-6b. Method B: The synthesis was carried out at 50 C for 30 min under microwave irradiation (300 W, 1 bar, Milestone start S microwave oven). Purification by column chromatography (initial eluent CH2Cl2, then CH2Cl2/MeOH = 40:1) afforded compounds 1-10a and 1-6b.

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. 696-07-1, 5-Iodouracil, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kraljevi?, Tatjana Gazivoda; Bistrovi?, Andrea; Dedi?, Matea; Paveli?, Sandra Kraljevi?; Sedi?, Mirela; Rai?-Mali?, Silvana; Tetrahedron Letters; vol. 53; 38; (2012); p. 5144 – 5147;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13036-57-2, 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. 13036-57-2, name is 2-Chloro-4-methylpyrimidine. A new synthetic method of this compound is introduced below.

A 1.3 M lithium hexadisilazide-THF solution (179 mL) was added dropwise to a mixture containing methyl nicotinate (16.0 g), 2-chloro-4-methylpyrimidine (15.0 g)and THF (179 mL) under a nitrogen atmosphere while maintaining the internal temperature at about -30 C., and the mixture was stirred at -30 C. for 30 minutes, and then at room temperature for 1 hour. A saturated ammonium chloride aqueous solution was added to the reaction mixture, and extraction was performed using ethyl acetate. Then, an organic layer was dried with anhydrous sodium sulfate and concentrated under a reduced pressure. The obtained residue was purified through silica gel column chromatography (elution solvent: ethyl acetate), and then solidified in methyl tert-butyl ether, and thereby 2-(2-chloropyrimidin-4-yl)-1-(pyridin-3-yl)ethan-1-one (19.2 g)as an orange solid was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13036-57-2, 2-Chloro-4-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; RIKEN; THE UNIVERSITY OF TOKYO; HASHIZUME, Yoshinobu; SEKIMATA, Katsuhiko; KUBOTA, Hirokazu; YAMAMOTO, Hirofumi; KODA, Yasuko; KOYAMA, Hiroo; TAGURI, Tomonori; SATO, Tomohiro; TANAKA, Akiko; MIYAZONO, Kohei; (156 pag.)US2019/337926; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 153435-63-3, 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. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine. A new synthetic method of this compound is introduced below.

Intermediate 50: 3-Fluoro-2-(pyrimidin-2-yl)benzoic acid.Step A: 3-Fluoro-2-(pyrimidin-2-yl)benzonitrile. 2-lodo-3- fluorobenzonitrile (2.5 g, 10.3 mmol) and 2-tributylstannane pyrimidine (3.7g, 10.0 mmol) were combined and dissolved in degassed DME (18 ml) then purged with bubbling N2 for 5 minutes. The reaction was treated withPd(PPh3)4 (577 mg, 0.5 mmol) and then purged with bubbling for 5 minutes in a sealed vessel and then heated in microwave at 160 C for 90 min. The reaction was cooled and filtered through celite and concentrated to minimum volume and the ppt the formed was diluted with hexanes (40 ml) and cooled to 0 C then filtered. The solid purified (FCC) (20-100% EA / hex) to give 3-fluoro- 2-(pyrimidin-2-yl)benzonitrile. 1 H NMR (400 MHz, CDCI3): 8.93 (d, J = 4.9 Hz, 2H), 8.14 (dd, J = 9.6, 2.7 Hz, 1 H), 7.86 (dd, J = 8.6, 5.3 Hz, 1 H), 7.36 (t, J = 4.9 Hz, 1 H), 7.32 – 7.24 (m, 1 H).

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; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1202759-91-8, 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. 1202759-91-8, name is N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine. A new synthetic method of this compound is introduced below.

Into a 25 ml, three neck flask under nitrogen atmosphere, a solution of N4-(3-aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine (0.15 g) in DMF (5 mL) was charged potassium 3-ethoxy-3-oxopropanoate (0.089 g), EDCI.HCl (0.117 g), HOBt (0.093 g) and TEA (0.164 g). The reaction mixture was stirred for 8 hr at room temperature. Completion of the reaction was monitored by TLC using hexane:ethyl acetate (5:5) as the mobile phase. After completion, the reaction mixture was poured into water. The product was extracted with ethyl acetate and the organic layer was washed with brine. The solvent was removed under reduced pressure at 40 C. The obtained solid was purified by triturating with diethyl ether (2×10 mL) to give 0.19 g of ethyl 3-((3-((5-fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)amino)-3-oxopropanoate. 1H NMR: DMSO-d6 (400 MHz): 1.182-1.234 (q, 3H, J=6.8), 3.306 (s, 3H), 3.461 (s, 2H), 3.623-3.646 (t, 2H, J=4.8), 4.010-4.033 (t, 2H, J=4.4), 4.090-4.144 (t, 2H, J=7.2), 6.775-6.797 (d, 2H, J=8.8), 7.267-7.283 (d, 2H, J=6.4), 7.511-7.533 (d, 1H, J=8), 7.575-7.591 (d, 1H, J=6.4), 7.817 (s, 1H), 8.058-8.066 (d, 1H, J=3.2), 8.963 (s, 1H), 9.375 (s, 1H), 10.162 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1202759-91-8, its application will become more common.

Reference:
Patent; Celgene Avilomics Research, Inc.; Tester, Richland; Chaturvedi, Prasoon; Zhu, Zhendong; Surapaneni, Sekhar S.; Beebe, Lisa; US2014/179720; (2014); A1;,
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. 139756-21-1, name is 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one. A new synthetic method of this compound is introduced below., COA of Formula: C17H20N4O2

EXAMPLE 21 5-(5-Bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one Bromine (0.93 g, 0.0058 mol) was added dropwise to a stirred solution of 5-(2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one (Preparation 7, 1.1 g, 0.00352 mol) in glacial acetic acid (20 ml). The mixture was stirred at 100 C. for 6.5 hours and the solvent was then removed by evaporation under vacuum. The residue was dissolved in a 9:1 mixture of methanol in dichloromethane (50 ml), and the solution washed with saturated aqueous sodium bicarbonate solution (50 ml), water (50 ml) and saturated brine (50 ml), then dried (MgSO4) and evaported under vacuum. The residue was chromatographed in silica gel (15 g) eluding with a mixture of methanol and dichloromethane (1:99) to give, after crystallisation from acetonitrile, the title compound (0.62 g, 45%), m.p. 157-159 C. Found C,52,41; H,5.25; N,14.01. C17 H19 BrN4 O2 requires C,52.18; H,4.89; N,14.32%.

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, 139756-21-1, 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one.

Reference:
Patent; Pfizer Inc.; US5272147; (1993); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia