Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 3435-25-4, 4-Chloro-6-methylpyrimidine, 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, HPLC of Formula: C5H5ClN2, blongs to pyrimidines compound. HPLC of Formula: C5H5ClN2

[0178] To a stirred solution of 4-chloro-6-methylpyrimidine (1 g, 7.77 mmol) in 1, 4- dioxane (30 mL) was added diisopropylethylamine (1.35 g, 10.50 mmol) and tert-butyl piperidin-4-ylcarbamate (1.7 g, 8.55 mmol). The reaction mixture was heated to 150 C and stirred for 3 h. After consumption of the starting materials (monitored by TLC), the mixture was diluted with water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified through silica gel column chromatography using 5% (0381) MeOH:DCM to afford tert-butyl (l-(6-methylpyrimidin-4-yl) piperidin-4-yl) carbamate (1.75 g, 77%) as an off-white solid. 1H-NMR (DMSO-< 5, 400 MHz): delta 8.34 (s, 1H), 6.69 (s, 1H), 4.28-4.24 (m, 2H), 3.54-3.52 (m, 1H), 3.00-2.93 (m, 2H), 2.23 (s, 3H), 1.77-1.75 (m, 2H), 1.38 (s, 9H), 1.30-1.22 (m, 3H); LC-MS: 293.3 (M+1); (column; X-Bridge C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.32 min. 5 mM NH4OAc: ACN; 0.80 mL/min); TLC: 50% (0382) EtOAc:hexanes (Rf. 0.2). The synthetic route of 3435-25-4 has been constantly updated, and we look forward to future research findings. Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/138689; (2015); A1;,
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Electric Literature of 33097-13-1, 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.33097-13-1, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C6H3Cl2N3S, molecular weight is 220.08, as common compound, the synthetic route is as follows.

[0301] Step 1 : To a suspension of 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (538 mg, 2.44 mmol) in DMF (4 mL) was added 6-aminoquinoline (388 mg, 2.69 mmol). After stirring at room temperature for 20 min, the mixture was diluted with water, the resulting precipitate was collected by filtration to give 4-chloro-2-(methythio)-6-(quinolin-6- yl)pyrimidin-5-carbonitrile (800 mg).

The chemical industry reduces the impact on the environment during synthesis 33097-13-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; XU, Qing; HUANG, Wolin; JIA, Zhaozhong J.; SONG, Yonghong; WO2012/61415; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 444731-75-3, N-(2-Chloropyrimidin-4-yl)-N,2,3-trimethyl-2H-indazol-6-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, SDS of cas: 444731-75-3, blongs to pyrimidines compound. SDS of cas: 444731-75-3

A 250-mL 3-necked flask equipped with a magnetic stir bar, thermometer, reflux condenser, and nitrogen inlet/outlet was charged with ethanol (60 ml_, 10 volumes), the product of Intermediate Example 4 (6.00 g, 20.85 mmol, 1.0 equiv) and 5-amino-2-rnethylbenzenesulfonamide (4.00 g, 21.48 mmol, 1.03 equiv) with stirring. The reaction mixture was heated to 70 0C. After stirring the reaction mixture at 68 – 72 0C for 3 hrs, 4M HCI in dioxane (0.11 mL, 0.44 mmol, 0.02 equiv) was charged over ca. 2 min. The reaction mixture was stirred at 68 – 72 0C until < 1.5% by area of the starting product of Intermediate Example 4 was remaining by HPLC analysis (Typically, this reaction is complete in > 8 hrs). The reaction mixture was cooled to 20 0C over ca. 30 min and stirred at 20 – 22 0C for 40 min. The product was then isolated by filtration and the filter cake washed with ethanol (20 mL, 3.3 volumes). The wet cake was dried under vacuum at 45 – 50 0C. The monohydrochloride salt of 5-({4- [(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]-pyrimidin-2-yl}amino)-2- methylbenzenesulfonamide (9.52 g, 96.4%) was isolated as a white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1 H), 8.55 (br s, 1 H), 7.81 (d, J = 6.2 Hz, 1 H), 7.75 (d, J = 8.7 Hz, 1 H), 7.69 (m, 1 H), 7.43 (s, 1 H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz, 1 H), 6.86 (m, 1 H), 5.74 (d, J = 6.1 Hz, 1 H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H), 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

The synthetic route of 444731-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/64753; (2007); A2;,
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Pyrimidine – Wikipedia

Synthetic Route of 5413-85-4 ,Some common heterocyclic compound, 5413-85-4, molecular formula is C4H3Cl2N3, 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.

Preparation of intermediate compound (50)a. To a stirred solution of 5-amino-4,6-dichloropyrimidine (48) (5 gm, 30.5 mmol) in DMSO (40ml) was added sodium sulfide (4.8 gm, 36.9 mmol) and stirred at room temperature for 12 h. The reaction mixture was diluted with water (40ml) and acidified with cone. HCl (1 ml). The solid obtained was collected by filtration washed with water and dried in vacuum to furnish 5-amino-6- chloropyrimidine-4-thiol (49) (4.09 gm, 83.13percent) as a brown solid, which was pure enough to be used for next step.

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; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; CHAND, Pooran; KOTIAN, Pravin, L.; KUMAR, V., Satish; WO2010/14930; (2010); A2;,
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Reference of 160199-05-3, 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. 160199-05-3, name is 2,4-Dichlorobenzo[4,5]thieno[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below.

Starting material2,4-dichlorobenzo [4,5] thieno [3,2-d] pyrimidine(32 g, 125.6 mmol)4,4,5,5-tetramethyl-2- (naphthalen-2-yl) -1,3,2-dioxaborolane(35 g, 138 mmol), Pd (PPh3) 4 (5.80 g, 5.02 mmol), K2CO3 (52 g, 376.41 mmol), THF (440 ml), water (220 ml)And the mixture is heated under reflux at 80 C to 90 C.When the reaction is complete, dilute with distilled water at room temperature and extract with methylene chloride and water.The organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallizationSub 2-61 (19.58 g, yield: 45%) was obtained

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,160199-05-3, its application will become more common.

Reference:
Patent; Duksan Neolux Co.,Ltd.; Jeong Ho-yeong; Ryu Jae-deok; Jeon Jin-bae; Cho Min-ji; (47 pag.)KR2019/1967; (2019); A;,
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Synthetic Route of 3993-78-0, 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 3993-78-0 as follows.

General procedure: To a round-bottom flask was charged with the correspondingaromatic halogen (1.0 equiv), the corresponding boronic acid(1.05-1.25 equiv), Pd(dppf)Cl2 (0.05 equiv) and base Na2CO3 (2.0equiv) under nitrogen atmosphere, then 1,4-dioxane (14 mL) andwater (2 mL) were added and the vessel was immediately sealed tightly. The resulting mixture was heated at 95 C for a period time (usually 2-6 h) until the completion of the reaction as monitoredby TLC. The cooled mixture was diluted with water and exhaustively extracted with ethyl acetate (30 mL 3). The organic phase was washed by brine, dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using ethyl acetate/petroleum ether as the eluent to afford the products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3993-78-0, its application will become more common.

Reference:
Article; Chen, Yadong; Dong, Ruinan; Duan, Chunqi; Huang, Jianhang; Jiang, Fei; Li, Hongmei; Li, Shuwen; Liu, Chenhe; Lu, Tao; Tang, Weifang; Wang, Xinren; Xu, Junyu; Zhang, Tianyi; Zhang, Yanmin; Zhu, Gaoyuan; Zhu, Yuqin; European Journal of Medicinal Chemistry; vol. 200; (2020);,
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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. Application In Synthesis of 6-Chloropyrimidin-4-amine

General procedure: To a solution of 6-chloropyrimidin-4-amine intoluene was added substituted amine (2.5 eq). The mixture was heatedat 105 C for 24 h and concentrated in vacuo. The residue was purifiedby flash column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5305-59-9, its application will become more common.

Reference:
Article; Yuan, Xinrui; Wu, Hanshu; Bu, Hong; Zheng, Peiyuan; Zhou, Jinpei; Zhang, Huibin; Bioorganic and Medicinal Chemistry; vol. 27; 7; (2019); p. 1211 – 1225;,
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Reference of 51674-77-2, Adding some certain compound to certain chemical reactions, such as: 51674-77-2, name is 4-Chloropyrido[3,2-d]pyrimidine,molecular formula is C7H4ClN3, 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 51674-77-2.

5 Intermediate 22 (50 mg, 0.151 rnmol), 4-chloropyrido[3,2-d]pyrimidine (37.5 mg,0.226 mmol), DIPEA (0.079 niL, 0.453 rnmol) and M-BUOH (1 mL) were combined and heated under microwave irradiation at 140C for 1 h. After cooling, the mixture was dissolved in EtOAc (100 mL) and washed with saturated brine (3 x 20 mL). The organic layer was separated, dried (MgS04), filtered and concentrated in vacuo. Purification by10 preparative HPLC gave the title compound (3.7 mg, 5%) as a white solid. 6H (DMSO- ^) 8.82-8.77 (2H, m), 8.44 (1H, s), 8.41 (1H, s), 8.07 (1H, dd, J 8.46, 1.52 Hz), 7.80 (1H, dd, J 8.46, 4.25 Hz), 7.63 (1H, dd, J 8.92, 6.31 Hz), 7.22 (1H, t, J9.13 Hz), 5.96 (2H, s), 5.82-5.75 (1H, m), 3.57-3.45 (4H, m), 3.44-3.37 (2H, m), 3.04-2.96 (2H, m), 2.47 (3H, d, J2.24 Hz), 1.55 (3H, d, J 6.71 Hz). LCMS (ES+) 461 (M+H)+, RT 2.50 minutes {Method15 2).

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. 51674-77-2, 4-Chloropyrido[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2011/58108; (2011); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 20781-06-0, 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.20781-06-0, name is 2,4-Diaminopyrimidine-5-carboxaldehyde, molecular formula is C5H6N4O, molecular weight is 138.1273, as common compound, the synthetic route is as follows.

General procedure: A mixture of 2-(benzo[d] thiazol-20-yl)acetonitrile 4 (1.0 mmol,0.17 g) and pyrimidine aldehyde 2 or 8 (1.0 mmol) was stirred at 25 C for 10-15 min in ethanol (10 ml) which contained piperidine (2.0 mmol, 0.2 ml). The reaction was monitored by TLC. The formed solid was filtrated and washed with hexane (2 x 10 ml) to give thecorresponding compounds 5 and 9a-d. 4.4.2.1 (E)-2-(Benzo[d]thiazol-2′-yl)-3-(2″,4″-diaminopyrimidin-5″-yl)acrylonitrile (5) Yellow powder; yield 77%; mp 280 C; IR (KBr, cm-1): 3395, 3307 (br, NH2), 2101 (CN), 2733 (C-H aliphatic), 1565 (C=C); 1H-NMR [DMSO-d6, 400 MHz]: (delta, ppm) 6.86-6.88 (bs, 2H, NH2, exchangeable with D2O), 7.47 (t, 1H, H5-benzothiazole, J = 8.0 Hz), 7.55 (t, 1H, H6-benzothiazole, J = 8.0 Hz), 8.05 (d, 1H, H4-benzothiazole, J = 8.0 Hz), 8.11 (d, 1H, H7-benzothiazole, J = 8.0 Hz), 8.30 (brs, 2H, NH2, exchangeable with D2O), 8.52 (s, 1H, H6-pyrimidine), 8.87 (olefinic H); 13C-NMR [DMSO-d6, 100 MHz]: (delta, ppm) 106.4 (C5-pyrimidine), 110.1 (C2′), 112.2 (CN), 122.3 (C7-benzothiazole), 133.3 (C4-benzothiazole), 139.9 (C5-benzothiazole), 139.9 (C6-benzothiazole), 153.1 (C3’a-benzothiazole), 160.0 (C6-pyrimidine), 161.5 (C3’b-benzothiazole), 162.9 (olefinic C), 164.5 (C4-pyrimidine), 164.8 (C2-benzothiazole), 167.1 (C2-pyrimidine); Anal. Calcd for C14H10N6S: C, 57.13; H, 3.42; N, 28.55; S, 10.89; Found: C, 57.18; H, 3.33; N, 28.63; S, 10.96; Anal. Calcd for C14H10N6S·2HBr: C, 36.86; H, 2.65; N, 18.42; S, 7.03; Found: C, 37.05; H, 2.45; N, 18.44; S, 7.05.

The chemical industry reduces the impact on the environment during synthesis 20781-06-0, I believe this compound will play a more active role in future production and life.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 56181-39-6, 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. 56181-39-6, name is 5-Bromo-4-chloropyrimidine. A new synthetic method of this compound is introduced below.

To a mixture of 5-bromo-4-chloro-pyrimidine (77 mg, 398 mumol) and (S)-2-amino-4-((2-(2,2-difluoroethoxy)ethyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoic acid (150 mg, 362 mumol) in THF (2 mL) H2O (0.5 mL) was added NaHCO3 (152 mg, 1.81 mmol) and the resulting mixture was heated to 70 C. for 2 h, cooled to rt, and then concentrated in vacuo to give the title compound that was used without further purification. LCMS (ESI+): m/z=571.3 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56181-39-6, 5-Bromo-4-chloropyrimidine, 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;,
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