Day: October 19, 2020

1004-40-6 , The common heterocyclic compound, 1004-40-6, name is 6-Amino-4-hydroxy-2-mercaptopyrimidine, molecular formula is C4H5N3OS, 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.

General procedure: A mixture of arylidene cyanoacetic acids 7 (10 mmol), uracil compound 1 (10 mmol) in nitrobenzene (15 mL) was stirred at 150oC for 2.5-4 h. After accomplishment of reac-tion (observed via TLC), the reaction mixture was cooled to room temperature and extra solvent was removed under vacuum. The performed solid was purified by recrystallization from ethyl acetate to afford 6-aminouracil-5-arylpropanenitriles 10 in good yields. The spectral data of products 10 are given below. 2.1.6.1. 3-(6-amino-4-oxo-2-thioxo-1,2,3,4-tetrahydro- pyrimidin-5-yl)-3-(4-hydroxyphenyl) propanenitrile 13a Gray powder. Yield = 87%. Mp = 222 – 225C.IR (cm-1), 3411 (OH), 3335,3280 (NH2), 3269, 3189 (2NH), 2221 (CN), 1671 (C=O amide); 1H NMR (500 MHz, DMSO-d6) delta 11.89 (s, 1H, NH exchangeable with D 2 O), 11.18 (s, 1H, NH exchangeable with D 2 O), 8.47 (s, 1H, OH exchangeable with D 2 O), 7.19 (d, J = 8.8 Hz, 2H), 6.97 (s, 2H, NH 2 ), 6.72 (d, J = 8.8 Hz, 2H), 4.27 (t, J = 5.6 Hz, 1H, CH), 2.90 – 2.84 (t, 2H, CH 2 ).13C NMR (125 MHz, DMSO-d6) delta 178.34, 157.53, 155.68, 151.99, 136.52, 129.28, 117.87, 115.70, 80.87, 38.51, 24.93; MS (m/z) = 288; Anal. Calcd for C 13 H 12 N 4 O 2 S: C, 54.16; H, 4.20; N, 19.43. Found: C, 54.36; H, 4.43; N, 19.28.

According to the analysis of related databases, 1004-40-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Al-Otaibi, Jamelah S.; Ibrahim, Diaa A.; El Gogary, Tarek M.; Letters in drug design and discovery; vol. 15; 12; (2018); p. 1240 – 1251;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

89793-12-4, 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. 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate, molecular formula is C7H7ClN2O2, 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.

Synthesis of Intermediate 4 [0270] Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95¡ã C. for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H2O (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50¡ã C. for 24 hr., yielding 896 g of compound 4 (solid, 86.8percent).

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. 89793-12-4, Ethyl 2-chloropyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Acetylon Pharmaceuticals, Inc.; Quayle, Steven Norman; Jones, Simon Stewart; US2015/150871; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3073-77-6, 2-Amino-5-nitropyrimidine, 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, 3073-77-6, blongs to pyrimidines compound. 3073-77-6

Example 83. iV-[4-(3-Pyrrolidiii-l-yl-propane-l-sulfonyl)-phenvI1-pyrimidine-2,5-diamine (52); [0244] To a solution of 2-amino-5-nitropyrimidine (350 mg, 2.5 mmol) in 20 mL anhydrous 1,4-dioxane were added intermediate 51 described in Example 82 (1.25 g, 3.76 mmol) in 5 mL anhydrous 1,4-dioxane, Xantphos, (289 mg, 0.5 mmol), Pd2(dba)3 (229 mg, 0.25 mmol) and Cs2CO3 (1.63 g, 5 mmol). The reaction mixture was stirred at 1000C for 5 h under argon. The reaction mixture was diluted with methanol and CH2Cl2 (5 mL each) then filtered. The filtrate was washed with brine. The organic phase was dried (Na2SO4) and the solvent was removed. The residue was dissolved in methanol and ethyl EPO acetate (2 mL each) and diluted with 20 mL hexane. The precipitated yellow-brown solid, was isolated by filtration and dried in vacuo (800 mg). The crude product was hydrogenated in 20 mL methanol using Pd/C (10 %, 500 mg) for 2 h. The palladium catalyst was removed by filtration, and the solvent was evaporated. The residue was dried in vacuo to yield the title compound (550 mg, 73 %), which was used without further purification.[0245] 1H NMR (DMSOd6): delta 1.60-1.68 (m, 6H)3 2.32 (m, 4H), 2.39 (m, 2H), 3.19 (m, 2H), 5.02 (bs, 2H), 7.68 (d, J= 9.0 Hz, 2H), 7.87 (d, J= 9.0 Hz, IH), 8.02 (s, 2H), 9.68 (s, IH). MS (ES+): m/z = 362 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 3073-77-6.

Reference:
Patent; TARGEGEN, INC.; WO2006/101977; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

3764-01-0, 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. 3764-01-0, name is 2,4,6-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

Intermediate 2; 2,6-dichloro-lambda/-methyl-4-pyrimidinamine ( Intermediate 3 4,6-dichloro-lambda/-methyl-2-pyrimidinamine; To a O0C mixture 2,4,6-trichloropyrimidine (0.50 g, 2.7 mmol) in THF (3 mL) was added methyl amine (2M THF, 3.0 mL, 6.0 mmol) dropwise. The reaction mixture was warmed to room temperature and stirred for 30 minutes, at which time LCMS indicated the formation of the desired product. The reaction mixture was treated with water (10 mL) and extracted with EtOAc (2×10 mL). The organics were washed with brine (10 mL), dried (Na2SO4), and evacuated. The crude material was purified by column chromatography (Gradient from 0-30% EtOAc in Hexanes) to afford 180 mg (1.01 mmol, 38%) of 2,6- dichloro-lambda/-methyl-4-pyrimidinamine and 150 mg (0.85 mmol 31 %) of 4,6-dichloro-lambda/- methyl-2-pyrimidinamine. MS (ES+) m/e 178 [M + H]+ for each.

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. 3764-01-0, 2,4,6-Trichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/105968; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

5177-27-5, 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. 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, the common compound, a new synthetic route is introduced below.

A solution of 3.2 g of 5-amino-2,4-dichloropyrimidine in 50 ml of ethyl acetate was added to a mixture of 25 ml of a saturated aqueous solution of sodium hydrogencarbonate and 25 ml of water. A solution of 4.9 g of 3,5-dimethyl-4-methoxybenzoyl chloride was added at room temperature over a period of 15 min, and the mixture was mixed intensively for 4 h. Then the layers were separated and the aqueous layer was extracted twice with ethyl acetate. After drying over sodium sulfate and filtration the solvent was removed in vacuo to give 7.54 g of raw product. The raw product was triturated with 25 ml of isopropanol. After filtration and washing with 10 ml of isopropanol 2.74 g of the title compound were obtained as a white solid.

Statistics shows that 5177-27-5 is playing an increasingly important role. we look forward to future research findings about 5-Amino-2,4-dichloropyrimidine.

Reference:
Patent; SANOFI; Kadereit, Dieter; Schaefer, Matthias; Hachtel, Stephanie; Dietrich, Axel; Huebschle, Thomas; Hiss, Katrin; US2013/72502; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

5413-85-4, 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. 5413-85-4, name is 5-Amino-4,6-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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.

Synthesis of Compound 11.1. A mixture of 4,6-dichloropyrimidin-5-amine (10 g, 6.09 mmol) and methyl amine (20 mL, 40% solution in water) in 1,4 dioxane was heated (80 C.). After 16 hr, the reaction mixture was cooled (0 C.), the solid was filtered, washed with water (2¡Á100 mL), and dried to afford compound 11.1 (8 g, 83%) as white solid. 1H-NMR (200 MHz, DMSO-d6) delta 7.73 (s, 1H), 6.82 (bs, 1H), 4.92 (bs, 2H), 2.87 (d, J=4.4 Hz, 3H). MS m/z 159 [M+1]+.

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. 5413-85-4, 5-Amino-4,6-dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunesis Pharmaceuticals, Inc; US2009/5359; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

2435-50-9, 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 2435-50-9 as follows.

To a stirred mixture of pyrimidine-4-carbaldehyde (2 g, 18.5 mmol, 1.0 eq.) and hydrazinecarbothioamide (2.02 g, 22.2 mmol, 1.2 eq.) in ethanol (20 mL) and water (20 mL) was added concentrated hydrochloric acid (100 iL) and the reaction heated at 70 C for 4 hours. After cooling to room temperature the precipitate was collected by filtration, washed with ethanol and then dried in air to afford 2-(pyrimidin-4- ylmethylene)hydrazinecarbothioamide as a brown solid (2.1 g, 62% yield). NMR (400 MHz, DMSO) 11.93 (IH, s), 9.21 (IH, d, J=1.3 Hz), 8.86 (IH, d, J=5.3 Hz), 8.59 (IH, s), 8.43 (IH, s), 8.39 (IH, dd, J=1.3, 5.3 Hz), 8.03 (IH, s).

The chemical industry reduces the impact on the environment during synthesis 2435-50-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

49845-33-2 , The common heterocyclic compound, 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine, molecular formula is C4HCl2N3O2, 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 2,4-dichloro-5-nitropyrimidine (500 mg, 2.5 mmol) dissolved in tetrahydrofuran (10 mL), sodium hydroxide (238 mg, 2.8 mmol) and aqueous ammonia (0.3 mL) was added, and reacted for 2 hrs at 55¡ãC. The solvent was removed under reduced pressure, and the residue was separated by flash column chromatography (dichloromethane: methanol=100:1), to obtain Compound w: 2-chloro-5-nitro-4-aminopyrimidine as a white solid (0.47 g, yield 84percent). MS(ESI)m/z: [M+H]+=175.

According to the analysis of related databases, 49845-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Huilun Life Science & Technology Co., Ltd; FAN, Xing; QIN, Jihong; (43 pag.)EP3284743; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5305-59-9, 6-Chloropyrimidin-4-amine, 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, 5305-59-9, blongs to pyrimidines compound. 5305-59-9

A mixture of 6-chloropyrimidin-4-amine (6.5 g, 0.050 mol), 4,4,5, 5-feframethyl-2-vinyl-l,3,2-dioxaborolane (9.24 g, 0.060 mol), fefrafc(triphenylphosphine)- palladium(O) (3.9 g, 0.0030 mol) and sodium carbonate (21 g, 0.20 mol) in dioxane (300 mL) and H20 (30 mL) was stirred at 90 C under nitrogen for 15 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between EtOAc (400 mL) and water (150 mL). The organic layer was separated, dried over Na2S04, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with DCM/MeOH (20: 1) to give the desired product as a white solid (4.8 g, 80% yield). LCMS (ESI) m/z: 122.1 [M+H+].

With the rapid development of chemical substances, we look forward to future research findings about 5305-59-9.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); 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. 1753-50-0, name is 2-Chloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., 1753-50-0

To a solution of (S)-2-amino-4-(((S)-2-fluoro-3-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoic acid hydrochloride (120 mg, 277 mumol) in THF (2 mL) and H2O (0.5 mL) was added NaHCO3 (70 mg, 831 mumol), and then 2-chloropyrimidine-5-carbonitrile (43 mg, 305 mol) and the resulting mixture was stirred at 70 C. for 1 h and then allowed to cool to rt. The mixture was adjusted to pH=6 by the addition of 1 M aq. HCl and then concentrated in vacuo. The crude residue was purified by reverse phase prep-HPLC to give the title compound. LCMS (ESI+): m/z=500.2 (M+H)+. 1H NMR (400 MHz, Methanol-d4) delta ppm 8.56 (br s, 1H) 8.45 (br s, 1H) 7.42 (br d, J=7.28 Hz, 1H) 6.52 (d, J=7.50 Hz, 1H) 4.75 (br d, J=3.31 Hz, 1H) 4.51 (t, J=5.84 Hz, 1H) 3.57 (d, J=3.97 Hz, 1H) 3.49-3.53 (m, 1H) 3.37-3.46 (m, 2H) 3.33-3.37 (m, 3H) 2.84-2.96 (m, 2H) 2.65-2.83 (m, 8H) 2.15-2.24 (m, 1H) 2.04-2.14 (m, 1H) 1.87-1.94 (m, 2H) 1.81 (br dd, J=13.78, 6.73 Hz, 2H) 1.58-1.69 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1753-50-0, 2-Chloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia