Category: pyrimidines

Synthetic Route of 1119280-66-8, 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.1119280-66-8, name is 2-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

1-Bromopropane (132 mg, 1.074 mmol) was added to a solution of product of Example 1001 (150 mg, 0.977 mmol) in DMF (10 mL) followed by cesium carbonate (0.477 g, 1.074 mmol), and the mixture was stirred at 25 C for 4 h. Insoluble solids were filtered off, and filtrate was concentrated. Residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using 5% ethyl acetate in hexane to afford title compound (0.15 g, 74.6%) as a brown color syrup. 1H NMR (300MHz, CDC13): delta 8.68 (s, 1H), 7.51 (d, J = 3.0 Hz, 1H), 6.62 (d, J = 2.7 Hz, 1H), 4.16 (t, J = 6.9 Hz, 2H), 1.91 (m, 2H), 0.94 (t, J = 7.5 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis 1119280-66-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; QIN, Donghui; CHEUNG, Mui; JOSHI, Hemant; TANGIRALA, Raghuram; BETHI, Sridhar, Reddy; WO2012/162129; (2012); A1;,
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

Under argon protection, the ice water was cooled, and 2-chloro-5-trifluoromethylpyrimidine (19 g, 104 mmol) was added to a 500 mL three-necked flask.Anhydrous tetrahydrofuran (100 mL) and tetrakistriphenylphosphine palladium (4.6 g, 4 mmol),The prepared compound 2 of tetrahydrofuran was poured into a constant pressure dropping funnel.The reaction solution was dropped (maintained at 20 C or lower). The reaction was carried out at room temperature overnight.Under ice bath, slowly add 10% ammonium chloride solution (300 mL) to quench the reaction.Ethyl acetate (300 mL) was added, and the black insoluble material was filtered off with Celite.The aqueous phase was extracted once more with ethyl acetate (200 mL).Wash with saturated brine, dry over anhydrous sodium sulfate, spin dry, sample, and purified by column chromatography.Obtained as a pale yellow liquid, compound 3 (25 g, 95 mmol, 91%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69034-12-4, 2-Chloro-5-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Jifeng Biological Technology Co., Ltd.; Xu Hongyan; Ma Jingxiang; (4 pag.)CN109988116; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2227-98-7, 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. 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine, molecular formula is C6H6N4, 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.

To a solution of 1 -((4RS, 5RS)-2,2-dimethyM-(methylthiomethyl)-1 ,3-dioxan-5-yl)-lambda/- methylmethanamine (30 mg, 137 mumol) in dioxane (2 mL) and water (0.5 mL) was added 9-deazaadenine (27.5 mg, 205 mumol) and 37% aqueous formaldehyde (15.86 mul,205 mumol). The reaction mixture was heated at 85 0C for 15 mins and then cooled and7N NH3ZMeOH (2.5 mL) was added. The solution was allowed to stand at RT for 3 days and concentrated to dryness. Chromatography (10% 7N NH3/MeOH in CH2CI2) gave 7-(((((4RS,5RS)-2,2-dimethyM-(methylthiomethyl)-1 ,3-dioxan-5- yl)methyl)(methyl)amino)methyl)-5H-pyrrolo[3,2-cdpyrimidin-4-amine (34 mg, 93 mumol,68 % yield) as a syrup. 1H NMR (CD3OD) delta 8.16 (1H, s); 7.45 (1H, s); 3.86 (1H, dd, J= 5.2, 11.9 Hz); 3.73-3.58 (3H, m); 3.52 (1 H1 dd, J = 10.6, 11.7 Hz); 2.79 (1 H, dd, J =2.5, 14.0 Hz); 2.53 (1H, dd, J = 7.1, 14.0 Hz); 2.32 (1H, dd, J = 5.5, 12.7 Hz); 2.24 (3H, s); 2.16 (1H, dd, J = 8.1 , 12.4 Hz); 2.06 (3H, s); 2.03-1.96 (1H, m); 1.36 (3H, s); 1.31(3H. s). 13C NMR (CD3OD) delta 152.6, 151.4, 147.8, 130.6, 115.7, 113.4, 100.1 , 75.9,64.7, 57.3, 52.4, 43.6, 39.3, 38.3, 29.9, 20.4, 17.4.

According to the analysis of related databases, 2227-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INDUSTRIAL RESEARCH LIMITED; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; WO2008/30118; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 36082-50-5, 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. 36082-50-5, name is 5-Bromo-2,4-dichloropyrimidine, molecular formula is C4HBrCl2N2, 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.

To a solution of 5-bromo-2, 4-dichloro-pyrimidine (1. 4 G) in acetonitrile (10 mL) at 0C was added triethylamine (0. 94 ML) and 3-AMINOPROPYLCARBAMIC acid-1,1- dimethylethyl ester (1.0 G). After removing the cooling bath the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated and to the residue water (20 ML) was added. The precipitate was collected, washed with water and ether to afford the title compound (1.8 g). ‘H NMR (400 MHz, DMSO-d6) : O/PPM = 1.34 (s, 9H), 1.62 (m, 2H), 2.93 (m, 2H), 3.36 (m, 2H), 6.78 (t, 1H), 7.64 (t, 1H), 8.22 (s, 1H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 36082-50-5, 5-Bromo-2,4-dichloropyrimidine.

Reference:
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/48343; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 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, 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. Safety of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

A mixture of 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide (32a) (0.20 g, 0.51 mmol) and 1-(ethoxycarbonylmethyl)piperazine (33) (0.17 g, 1.01 mmol) in 4 mL of EtOH was heated with a CEM Discover microwave at 250 W, Pmax 150 C. for 45 min. The resulting mixture was treated with EtOH (6 mL) and then stirred at rt for 1 h. The solid was collected on a filter to give 0.24 g of ethyl 2-(4-(6-(5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-ylamino)-2-methylpyrimidin-4-yl)piperazin-1-yl)acetate (34a) (89% yield). HPLC>99% pure (Rt 2.517 min); LC/MS (ES-) 530/532 (M+H, 100); 1H NMR (DMSO-d6) delta 11.48 (s, 1H), 9.86 (s, 1H), 8.22 (s, 1H), 7.40 (m, 1H), 7.28 (m, 2H), 6.06 (s, 1H), 4.10 (q, J=7.1 Hz, 2H), 3.53 (s, 4H), 3.29 (s, 2H), 2.59 (t, J=4.6 Hz, 4H), 2.41 (s, 3H), 2.24 (s, 3H), 1.20 (t, J=3H); Anal. Calcd for C24H28ClN7O3S: C, 54.38; H, 5.32; Cl, 6.69; N, 18.50; S, 6.05. Found:: C, 54.24; H, 5.16; Cl, 6.80; N, 18.59; S, 6.09.HPLC conditions column: YMC ODS-A S5 4.6×50 mm; UV: 220 nm; gradient time: 4 min; flow rate: 4 mL/min, 0-100% B; solvent A: 10% MeOH/90% H2O with 0.2% H3PO4, solvent B: 90% MeOH/10% H2O with 0.2% H3PO4.

With the rapid development of chemical substances, we look forward to future research findings about 302964-08-5.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/219370; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 23002-51-9, 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. 23002-51-9, name is 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, 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.

Preparation No.3: l/7-Pyrazolo[3,4-Patent; ABBOTT LABORATORIES; WOLLER, Kevin R.; CURTIN, Michael L.; FRANK, Kristine E.; JOSEPHSOHN, Nathan S.; LI, Biqin C.; WISHART, Neil; WO2011/156698; (2011); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1088994-22-2, 5-Methyl-2-(pyrimidin-2-yl)benzoicacid, 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: C12H10N2O2, blongs to pyrimidines compound. HPLC of Formula: C12H10N2O2

2- { 2- ((2R,5R)-5 – ( [Y5~Fiuoropyridin-2 -vDoxyjmethyl } -2-methy Ipiperidin- 1 -vDcarbonyl] -4- methylphenvUpyrimidine (5To a 2 L round bottom flask, equipped with over head stirrer, thermocouple, dropping funnel, and nitrogen inlet, was charged biaryl acid 3 (43.10 g, 1.05 equiv), 2,6- dimethylpyridine (23.15 mL, 1.05 equiv) and DMF (250 mL, 5 V) and was cooled to 5 C. Then, trimethyl acetyl chloride (Piv-Cl) (24.45 mL) was slowly added at 5-10 C. The reaction was stirred at 10 C for 0.5 h. Amine-HCl salt 4 (50.00 g) and 50 wt% T3P in DMF (5.96 g, 5 mol%) were added at 10-15 C, respectively. The reaction mixture was stirred at 20-25 C for 1- 2 h (typical > 76 A% conversion), 2,6-lutidine (22.05 mL, 1.0 equiv) was slowly added over 0.5 h, the reaction mixture was stirred at rt for 3-5- h (> 95 A% conversion). The reaction can be also carried out as follows. To a 2 L round bottom flask, equipped with overhead stirrer, thermocouple, dropping funnel, and nitrogen inlet, was charged biaryl acid 3 (43.10 g, 1.05 equiv), 2,6-dimethylpyridine (45.2 mL, 2.05 equiv), amine-HCl salt 4 (50.00 g), 50 wt% T3P in DMF (5.96 g, 5 mol%)and DMF (250 mL, 5 V) and the resulting mixture was cooled to 15 C. Then, Piv-Cl (24.45 mL) was slowly added at 15-25 C. After complete addition of Piv-Cl, the reaction mixture was aged at 20-25 C for 3-5 h (>95 A% conversion).10 mol% of 2,6-lutidine (2.21 mL) and 10 mol% of Piv-Cl (2.45 mL) were added at rt, respectively. The reaction mixture was stirred at room temperature for 8-16 h (98.5 A% conversion). The reaction mixture was diluted with toluene (500 mL, 10 volume) and water (250 mL, 5 V) at 10-20 C. The reaction mixture was stirred at 10-20 C for 0,5 h. After phase separation, the aqueous layer was extracted with toluene (250 mL x 1, 5 volumes). The combined organic layer was washed with water (200 mL x 1, 4 volumes), 1 N NaOH (200 mL x 1, 4 volumes), and 16% brine (100 mL x 1, 2 volumes).The resulting toluene solution was filtered through 20 wt% of Aquagard activated carbon (14.8 g, equal to 20 wt% of assay product), which was held on solka flock (16 g). The cake was rinsed with toluene (400 mL, 8 volumes)The combined filtrates were concentrated to 150 mL (total volume). At this point, tert-butylbenzene (70 mL) was added dropwise. The resulting solution was solvent-switched to tert-butylbenzene (200 mL, total volume). Crystalline solid 5 was formed during solvent-switch. The resulting slurry was heated to 90-95 C to become homogenous solution. The resulting solution was cooled to 80 C and was seeded with 2% desired crystalline form of 5. The slurry was aged at 80 C for 2 h, and then was slowly cooled to 60 C over 10 h, and from 60 to 20 C over 10 h. The resulting slurry was aged at 20 for 24-48 h. The crystalline solid was collected by filtration, rinsed with tert-butylbenzene (50 mL), n-heptane (100 mL), dried under vacuum with nitrogen sweep and gave 2-{2-[((2ii,5ii)-5-{[(5-fiuoropyridin-2-yl)oxy]methyl}-2- methylpiperidin-l-yl)carbonyl]-4-methylphenyl}pyrimidine (5) (66.85 g, 88% isolated yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1088994-22-2, 5-Methyl-2-(pyrimidin-2-yl)benzoicacid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; FENG, Yun Shao; MOSES, Anthony; ZHONG, Yong-Li; WO2012/58129; (2012); 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. 289042-12-2, name is tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate, the common compound, a new synthetic route is introduced below. Safety of tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

A solution of the compound of formula (39) (7.0 g, 12.1 MMOL) and CAMPHOR-1 0-SULFONIC ACID (2.4 g, 10.4 MMOL) in acetonitrile (50 ml) and water (5 ml) is stirred at room temperature for 30 minutes. It is then diluted with ether and washed successively with saturated sodium hydrogen carbonate solution and brine. The organic phase is dried (using NA2SO4). The salt mixture is filtered off and the filtrate obtained is concentrated by evaporation. The concentrated crude product is dissolved in ethyl acetate and made to crystallise by adding hexane. In that manner, 1.6 G (57 %) of the desired product (41) can be obtained in the form of colourless crystals. ‘H NMR (300 MHz, DMSO-DE) : 1.22 (d, J = 6.7 Hz, 6H); 1.32-1. 44 (m, 1H) ; 1. 38 (s, 9H); 1.49-1. 59 (m, 1H); 2.20 (dd, J = 15.0, 7.9 Hz, 1H); 2.28 (DD, J = 15.0, 5.3 Hz, 1H); 3.39-3. 47 (m, 1H) ; 3.44 (s, 3H); 3.53 (s, 3H); 3.74-3. 85 (M, 1H) ; 4.14-4. 22 (m, 1H) ; 4.64 (d, J = 5.3 Hz, 1H) ; 4.89 (d, J = 4.7 Hz, 1H) ; 5.51 (dd, J = 16.1, 5.6 Hz, 1H) ; 6.51 (dd, J = 16. 1,1. 2 Hz, 1H) ; 7.25 (dd, J = 8.8, 8.8 Hz, 2H); 7.70 (dd, J = 9.1, 5.6 Hz, 2H). 13C NMR (75 MHz, DMSO-DB) : 22.4, 28.6, 32.1, 34.0, 42.4, 44.4, 44.9, 65.9, 69.2, 80. 2, 115.7 (JCF = 21.7 Hz), 122.1, 122.4, 132.8 (JCF = 8.7 Hz), 135.1 (JCF = 3.2 Hz), 141.9, 157.4, 163.2 (JCF = 249 Hz), 163.4, 171.1, 174.9. HPLC: CHIRALCEL OD (0.46×25 cm), hexane: EtOH 95: 5,1 ml/min, TR = 19.2 min, S 98 % ee.

The synthetic route of 289042-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CIBA SPECIALTY CHEMICALS HOLDING INC.; WO2004/103977; (2004); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 7752-82-1, 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. A new synthetic method of this compound is introduced below.

In the 500 ml round bottom flask in three adding 2 – amino -5 – bromo pyrimidine (10.44g, 60mmol), joint boric acidfrequency that alcohol ester (19.05g, 75mmol), acetonitrile 300 ml, potassium acetate (17.67g, 180mmol), Pd (dppf) Cl2.CH2Cl2 (2.45g, 3mmol). The mixture of the reaction bottle 85 C stirring for 6.5 hours. TLC and HPLC to determine the completion of reaction. After the reaction, steaming and to remove the solvent, to obtain crude product, crude methylene chloride: hexane=1:3 beating, then ethyl acetate recrystallization to obtain the pure product 2 – amino pyrimidine -5 – boric acid frequency which ester borate, after drying, calculating yield 80%, purity 99.45% (HPLC).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7752-82-1, its application will become more common.

Reference:
Patent; Shandong Youbang Biochemical Technology Co., Ltd.; Cheng Wei; Geng Xuanping; Wang Lei; Lai Xinsheng; Lai Chao; Lai Ziteng; (5 pag.)CN106632443; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1044145-59-6, Adding some certain compound to certain chemical reactions, such as: 1044145-59-6, name is (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol,molecular formula is C6H7ClN2OS, 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 1044145-59-6.

To a solution of KR-i 8 (i .7 g, 9 mmol) in 0H2012 (20 mL) was added TBSCI(tert-Butyldimethylsilyl chloride) (2.0 g, i3.3 mmol), imidazole (i .2 g, i8mmol). The reaction mixture was stirred at r.t. for iO h. The reaction mixturewas quenched into water, extracted with 0H2012, dried with anhydrousNa2SO4, concentrated to give the crude product which was purified by column chromatography (eluting with PE/ EA = iOO:i to 5:i) to give the pure reagent KR-19 (2.1 g, 77.8%) as a yellow solid. ESI-MS (Mi-i): 305.1 calc. for C12H21CIN2OSSi: 304.0.

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. 1044145-59-6, (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUNDACION PARA LA INVESTIGACION MEDICA APLICADA; CUADRADO TEJEDOR, Maria Del Mar; FRANCO FERNANDEZ, Rafael; GARCIA OSTA, Ana Maria; OYARZABAL SANTAMARINA, Julen; RABAL GRACIA, Maria Obdulia; WO2014/131855; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia