Tag: M.W:100-200

Application of 6623-81-0 , The common heterocyclic compound, 6623-81-0, name is 2,4-Dihydroxy-5-methoxypyrimidine, molecular formula is C5H6N2O3, 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.

Compound 110: To a solution of compound 109 (1.42 g, 10 mmol) in dry acetonitrile (30 mL) was added BSA (10.5 g, 50 mmol). The reaction mixture was stirred at 60 C for 4 h and cooled to room temperature. To the reaction mixture were added compound 103 (5.04 g, 10 mmol) and TMSOTf (2.7 mL, 15 mmol). The resulted reaction mixture was stirred at 60 C for 4 h. Upon completion of the reaction as monitored by TLC, the reaction mixture was treated with methylene chloride and saturated sodium bicarbonate. The organic phase was separated, and the aqueous phase was extracted with methylene chloride. The combined organic phase was dried over anhydrous Na2SO4. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column giving 3.8 g desired compound 110 in 65% yield.

The synthetic route of 6623-81-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roy, Atanu; Conlee, Christopher R.; De Fougerolles, Antonin; Fraley, Andrew W.; EP2918275; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 69034-12-4 , The common heterocyclic compound, 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, 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.

Step 6: To a stirred mixture of B-1.19 (1.88 g, 9.29 mmol) and DIPEA (2.50 mL, 14.6 mmol) in NMP (20 mL) is added at RT under a nitrogen atmosphere B-1.20 (2.20 g, 12.1 mmol). The mixture is stirred in microwave at 100C for 30 min. The mixture is poured into H20 and extracted with EA. The organic phase is separated, washed with citric acid (10% aq. solution) and H20. The organic layer is dried and concentrated. The residue is purified by flash column chromatography on silica gel (using a solvent mixture of n-hexane/EA 80/20) to get 2.7 g of B- 1.21. ESI-MS: 349 [M+H]+; HPLC (Rt): 1.34 min (method P).

The synthetic route of 69034-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; SCHEUERER, Stefan; (69 pag.)WO2017/178341; (2017); A1;,
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Synthetic Route of 4595-61-3 ,Some common heterocyclic compound, 4595-61-3, molecular formula is C5H4N2O2, 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) 5-pyrimidyl carboxylic acid, 1.9 gm, was added to 30 ml of methylene chloride. 2.4 gm of carbonyldimidazole was added to the system. The system was stirred at room temperature for 3 hours to form the 5-pyrimidyl carboxylic acid imidazolide.

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. 4595-61-3, Pyrimidine-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chevron Research Company; US4504484; (1985); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 69034-12-4, 2-Chloro-5-(trifluoromethyl)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, name: 2-Chloro-5-(trifluoromethyl)pyrimidine, blongs to pyrimidines compound. name: 2-Chloro-5-(trifluoromethyl)pyrimidine

A solution of example 72a (12.2 g, 33.9 mmol), Nu,Nu-Diisopropylethylamine (11.6 ml, 67.8 mmol) and 2-Chloro-5-(Trifluoromethyl)pyrimidine (6.8 g, 37.3 mmol) in 100 ml of anhydrous DMSO is heated at 100C and stirred 30 minutes. After cooling to room temperature, water is added and the new formed precipitate is filtered and washed with water and with n-hexane. The solid is dissolved in EtOAc and washed with 10% aqueous citric acid solution; the organic layer is separated, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue is suspended in diethylether and filtered; then the resulting solid is purified by silica flash chromatography, using cyclohexane/EtOAc 1 : 1 to 20:80 as eluent, to obtain the title compound (15.0 g, 88% yield). HPLC-MS (Method 10): Rt MS (ES+): m/z = 505 [M+H]+ Chiral HPLC (Method 9): Rt = 10.88 min

The synthetic route of 69034-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); 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.1005-37-4, name is 6-Chloro-N4-methylpyrimidine-2,4-diamine, molecular formula is C5H7ClN4, molecular weight is 158.59, as common compound, the synthetic route is as follows.name: 6-Chloro-N4-methylpyrimidine-2,4-diamine

To a mixture of beta-chloro-Lambda^-methyl^^-pyrimidinediamine (500 mg, 3.15 mmol), 2-acetyl- 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,2-dihydroindazolo[4,3- 6c][1 ,5]benzoxazepine (1.60 g, 4.10 mmol), tricyclohexylphosphine (22 mg, 0.08 mmol), and K2CO3 (1.31 g, 9.45 mmol) in 1 ,4-dioxane (4 mL) and water (6 mL) was added Pd2(dba)3 (27 mg, 0.03 mmol) under nitrogen, and the reaction mixture was heated for 40 minutes at 140 0C in a microwave reactor. The mixture was cooled to room temperature and filtered, and the resulting solid was washed with EtOAc and purified by reverse phase chromatography (gradient: 30% CH3CN/H2O to 40% CH3CN/H2O w/0.5% TFA) to afford a TFA salt of the title compound (169 mg, 16%) as a yellow solid. LC-MS (ES) m/z = 346 [M+H]+. 1H NMR (400 MHz, DMSOd6): delta 2.95 – 2.96 (d, J = 4.4 Hz, 3H), 6.46 (s, 1 H), 6.89 – 6.97 (m, 1 H), 7.03 (s, 1 H), 7.07 – 7.11 (m, 1 H), 7.26 – 7.30 (m, 2H), 7.47 (s, 1 H), 8.74 (bs, 1 H), 9.65 (s, 1 H), 12.14 (bs, 1 H), 12.68 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1005-37-4, 6-Chloro-N4-methylpyrimidine-2,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; BRADY, Gerald, Patrick, Jr.; GALLAGHER, Timothy, Francis; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; WO2010/120854; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3073-77-6, name is 2-Amino-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C4H4N4O2

EXAMPLE 105. Synthesis of (5-Nitro-Pyrimidin-2-vI)-Phenyl-Amine (Intermediate54154[0306] A suspension of 5-nitro-pyrimidin-2-ylamine (0.10 g, 0.71 mmol), bromobenzene (0.15 g, 0.96 mmol), Pd(OAc)2 (13 mg, 0.057 mmol), Xantphos (67 mg, 0.12 mmol) and potassium tert-butoxide (0.22 g, 2.0 mmol) in DMF (3 mL) was sealed in a microwave reaction tube and irradiated with microwave at 140 0C for 15 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the crude product used in the next step without further purification.

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, 3073-77-6, 2-Amino-5-nitropyrimidine.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 14394-60-6 ,Some common heterocyclic compound, 14394-60-6, molecular formula is C5H6ClN3, 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) 6-methyl-2-(2,2,2-trifluoroethoxy)pyrimidin-4-amine To a stirred solution of 2-chloro-6-methylpyrimidin-4-amine (718 mg, 5.00 mmol, CAS 14394- 60-6) in THF (10 mL) was added NaH (240 mg, 60% in mineral oil, 6.0 mmol) at room temperature. After 30 minutes, 2,2,2-trifluoroethanol (500 mg, 5.00 mmol, CAS 75-89-8) was added and the mixture was heated to 75 C for 16 hours before being partitioned between water and EtOAc. The layers were separated and the organic phase was washed with brine, dried(Na2S04) and concentrated in vacuo to afford the title compound as white solid which was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14394-60-6, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CECERE, Giuseppe; GALLEY, Guido; NORCROSS, Roger; PATINY-ADAM, Angelique; PFLIEGER, Philippe; (68 pag.)WO2016/30306; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3177-24-0, 2,4-Dichloropyrimidine-5-carbonitrile, 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, 3177-24-0, blongs to pyrimidines compound. name: 2,4-Dichloropyrimidine-5-carbonitrile

[00607] General conditions for the preparation of 2-amino-4-chloropyrimidine-5-carbonitrile:[00608] To a solution of 2,4-dichloropyrimidine-5-carbonitrile (E-1) (2.0 g, 11.5 mmol) in 1,4-dioxane (20 mL) at 0 °C, ammonium hydroxide (28-30percent, 4.4 mL, 34.5 mmol) is added dropwise, and the resulting mixture is stirred while warming from 0 °C to RT for 2 h. Then, the mixture is partitioned between ethyl acetate (200 mL) and water (50 mL). The organic layer is washed with brine, dried over Na2SO4 and filtered. The filtrate is mixed with silica gel and then concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0- 100percent ethyl acetate/hexanes to afford the product (E-2) (917 mg) and a mixture of (E-2) and (E-3). Additional (E-3) can be obtained from this mixture by a second column chromatographic purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2015/168079; (2015); 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.115617-41-9, name is 4,5-Dichloro-6-ethylpyrimidine, molecular formula is C6H6Cl2N2, molecular weight is 177.03, as common compound, the synthetic route is as follows.Recommanded Product: 115617-41-9

EXAMPLE 7 5-Chloro-6-ethyl-4-[cis-4-(isopropenyl)cyclohexylamino]pyrimidine (alternative synthesis) 1.6 g (0.009 mol) of 4,5-dichloro-6-ethylpyrimidine and 1.2 g (0.009 mol) of 4-isopropenylcyclohexylamine were stirred with 1.8 g (0.013 mol) of K2 CO3 in 10 ml of DMF at 80 C. for 6 hours. After cooling to room temperature, the mixture was placed in water and extracted with ether. The organic phase was washed with water, dried and filtered, and the filtrate was chromatographed on silica gel with petroleum ether/ethyl acetate 7:3 in order to separate the cis/trans isomers. The cis-cyclohexylamino derivative is eluted first (1.4 g, yellow oil) followed by the trans-cyclohexylamino derivative (0.6 g, yellow oil).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,115617-41-9, 4,5-Dichloro-6-ethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Hoechst-Schering AgrEvo GmbH; US5889012; (1999); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 7752-72-9, 5-Chloro-6-methylpyrimidin-4(3H)-one, 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, Application In Synthesis of 5-Chloro-6-methylpyrimidin-4(3H)-one, blongs to pyrimidines compound. Application In Synthesis of 5-Chloro-6-methylpyrimidin-4(3H)-one

2) The Preparation of Intermediate 4,5-dichloro-6-methylpyrimidine 50 ml of POCl3 was added dropwise to a solution of 14.5 g (0.1 mol) of 4-hydroxyl-5-chloro-6-methylpyrimidine in 50 mL of toluene, the mixture was refluxed for 5-7 h after addition. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was concentrated under reduced pressure to remove toluene and extra POCl3, and then poured into ice water. The water phase was extracted with ethyl acetate (3*50 ml), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column to give 14.43 g as yellow liquid with yield of 88.5%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7752-72-9, 5-Chloro-6-methylpyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; SINOCHEM CORPORATION; Liu, Changling; Guan, Aiying; Lan, Jie; Wang, Lizeng; Wang, Bin; Zhu, Minna; Sun, Qin; Ren, Weijing; Feng, Cong; Ren, Lanhui; Chai, Baoshan; Li, Zhinian; US2015/225378; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia