Pyrimidines

Electric Literature of 2227-98-7, Adding some certain compound to certain chemical reactions, such as: 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine,molecular formula is C6H6N4, 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 2227-98-7.

[0088] (2R)-2-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3- (pyrazin-2-ylsulfanyl)propan-l-ol (V.2). Compound V.l (0.220 g, 0.68 mmol) was dissolved in CH2CI2 (8 mL) and trifluoroacetic acid (2 mL) added. After 2 h the solvent was evaporated and the residue dissolved in MeOH (10 mL) and neutralized with Amberlyst A21 resin then passed through a short column of the same resin and eluted with MeOH. The fractions containing product were evaporated to a yellow gum that was dissolved in tert-butanol (4 mL) then aq. formaldehyde solution (37%, 0.061 mL, 0.81 mmol) and 9-deazaadenine (0.091 g, 0.68 mmol) were added and the mixture heated at 70 C for 16 h. Silica gel was added to absorb all the solvent then the solvent was evaporated and the residue chromatographed on silica gel (gradient of 10 – 15% 7M NH3/MeOH in CHCI3) to give V.2 as a colourless solid (0.055 g, 25%). XH NMR (500 MHz, CD3OD): delta 8.35 (d, J = 1.5 Hz, 1H), 8.28 (dd, J = 2.6, 1.7 Hz, 1H), 8.14 (d, J = 2.1 Hz, 1H), 8.12 (s, 1H), 7.43 (s, 1H), 4.05 (d, J = 13.9 Hz, 1H), 4.02 (d, J = 13.8 Hz, 1H), 3.74 (dd, J = 11.3, 4.9 Hz, 1H), 3.64 (dd, J = 11.3, 5.5 Hz, 1H), 3.39-3,31 (m, 2H + residual deuterated solvent), 3.01-2.97 (m, 1H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 158.2 (C), 152.0 (C), 150.8 (CH), 146.5 (C), 145.2 (CH), 144.6 (CH), 140.3 (CH), 129.0 (CH), 115.4 (C), 114.7 (C), 63.7 (CH2), 58.4 (CH), 41.4 (CH2), 31.6 (CH2). ESI-HRMS calcd Ci4H18N7OS+ (M+H)+, 332.1289, found 332.1287.

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. 2227-98-7, 4-Aminopyrrolo[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; SCHRAMM, Vern, L.; CLINCH, Keith; GULAB, Shivali, Ashwin; WO2015/123101; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 23002-51-9, 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. 23002-51-9, name is 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

Example 19 Methanesulfonyl-piperidin-4-yl)-(1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine To a stirred solution of (1-methanesulfonyl-piperidin4-yl)-(1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amine (Example 18, 61 mg, 0.40 mmol) in DMF (2.5 mL), sodium bicarbonate (60 mg) and 1-methanesulfonyl-piperidin-4-ylamine(85 mg, 0.48 mmol) were added and the mixture was stirred at 100 C. for 5 hours. The solvent was removed under reduced pressure and the residue was treated with water and the mixture was extracted with EtOAc. The extract was dried with sodium sulfate and concentrated to give a solid, which was purified by reverse phase HPLC to give an off-white solid. 29 mg, 29%. MS (M+H)+, 297.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23002-51-9, 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Roberts, John Lawson; US2005/277655; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 90213-67-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 90213-67-5, name is 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(2S,35)-ethyl 3 -aminobicyclo[2.2.2]octane-2-carboxylate hydrochloride (1.26 g, 5.40 mmol) and 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (1.10 g, 5.40 mmol) were dissolved in DMF (5 mL), then potassium carbonate (1.50 g, 11.00 mmol) was added. The mixture was stirred at rt overnight. Water (50 mL) was added to quench the reaction, and the resulting mixture was extracted with EtOAc (50 mL x 2). The combined organic phases were washed with saturated brine (80 mL), dried over anhydrous Na2504, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 10/1) to give the title compound as a yellow solid (979 mg, 50 %).MS (ESI, pos.ion) m/z: 363.2 [M+H]?H NMR (400 MHz, CDC13) (ppm): 6.87 (d, J= 3.4 Hz, 1H), 6.41 (s, 1H), 5.32 (s, 1H), 4.63 (s, 1H), 4.21 (q, J= 7.1 Hz, 2H), 3.76 (s, 3H), 2.39 (d, J 4.9 Hz, 1H), 1.96 – 1.52 (m, 1OH), 1.26 (t, J 7.0 Hz, 3H).

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 90213-67-5, 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; REN, Qingyun; TANG, Changhua; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (215 pag.)WO2018/127096; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1114560-76-7, 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. 1114560-76-7, name is 4-Bromo-2-methylpyrimidine. A new synthetic method of this compound is introduced below.

Example 46a 6-Methoxy-5-(2-methyl-pyrimidin-4-yl)-pyridin-2-ylamine PdCl2(PPh3)2 (413 mg, 0.58 mmol) was added to a degassed mixture of 4-bromo-2-methyl-pyrimidine (1.02 g, 5.89 mmol), 6-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine 2 (Example 7c, 2.2 g, 8.79 mmol) and K2CO3 (2.43 g, 17.6 mmol) in a mixture of DME, EtOH and H2O (6:2:1, 200 mL). The reaction mixture was heated in a sealed tube for 1 hour at 100 C. The mixture was cooled to room temperature, diluted with ethyl acetate and filtered. The volatiles were removed in vacuo and the residue was purified by flash column chromatography using a gradient of 5 to 10% EtOAc in DCM to afford 610 mg (48%) of the title compound. 1H NMR (400 MHz, CD3OD) delta ppm 2.74 (s, 3H) 4.06 (s, 3H) 6.29 (d, 1H) 8.27 (d, 1H) 8.45 (d, 1H) 8.55 (d, 1H). ESMS m/z 217.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1114560-76-7, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2012/122843; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3680-69-1, 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.3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

A suspension of 4-chloro-7H-pyrrolo[2,3-d]pyri- midine (1.54 g, 10 mmol) and Pd(PPh3)4(ii6 mg, 0.100 mmol) in THF (10.0 mE, iM) was vacuum purged with N2. Then a solution of dimethylzinc (3.82 g, 40.0 mmol, 20.0 mE, 2M in toluene) was added and the mixture was vacuum flushed with N2 and then heated to 60 C. for 16 h. ECMSAPC1(+) showed .-i:i mixture of starting material to product. The reaction was heated to 80 C. for another 24 h, in which ECMS showed a 2: 1 mixture of product to starting material. The reaction mixture was cooled in an ice-water bath then quenched with saturated NaHCO3 (aq) and extracted with EtOAc. The EtOAc was washed with brine, dried with Mg504, filter and concentrated to an oil. The crude material was purified by ISCO-Rf on a 24 g column eluting with 0-100% EtOAc-Heptane to give compound V-1 (561 mg, 42%). ECMS [M+i] 134; ?HNMR (400 MHz, CDC13) oe ppm8.94 (s, iH), 7.42 (d, J=3.4 Hz, iH), 6.68 (d, J=3.4 Hz, iH),2.87 (s, 3H)

Statistics shows that 3680-69-1 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; Pfizer Inc.; Tatlock, John Howard; McAlpine, Indrawan James; Tran-Dube, Michelle Bich; Rui, Eugene Yuanjin; Wythes, Martin James; Kumpf, Robert Arnold; McTigue, Michele Ann; (181 pag.)US2016/244475; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 84905-80-6, 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.84905-80-6, name is 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

(i) Production of {4-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]phenyl}methanol 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (307 mg) was dissolved in N,N-dimethylformamide (2 mL), potassium carbonate (304 mg) was added, and the mixture was stirred at room temperature for 30 min. 4-Hydroxymethylbenzyl chloride (377 mg) was added, and the mixture was stirred at room temperature for 16 hrs. After diluting with water (30 mL), the mixture was extracted with ethyl acetate/tetrahydrofuran (3:1, 80 mL*2). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20 ? 0:100) to give the title compound (383 mg) as a powder. 1H-NMR(CDCl3) delta: 2.15 (1H, br s), 4.69 (2H, d, J= 4 Hz), 5.71 (2H, s), 6.76 (1H, m), 7.06 (2H, d, J= 8 Hz), 7.34 (2H, d, J= 8 Hz), 7.50 (1H, d, J= 3 Hz), 8.69 (1H, s).

Statistics shows that 84905-80-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1752457; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 59549-51-8, name is 5-Bromo-2-chloro-4-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H4BrClN2S

To5-bromo-2-chloro-4-(methylthio)pyrimidine (3 g, 12.53 mmol) in dioxane (12.53 mL) was added 2-methylpropan-2-amine (7.93 mL, 75 mmol). The mixture was stirred at 100 C overnight in a sealed vessel. The solvent was removed under reduced pressure and the residue was dissolved in 100 mL ethyl acetate and washed with 50 mL of a 1M aqueous solution of sodium hydrogen phosphate. The aqueous layer was back-extracted with 50 mL ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give 5-bromo-N-tert-butyl-4-(methylthio)pyrimidin-2- amine (3.4 g, 12.31 mmol, 98% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.61 – 8.72 (m, 1 H), 8.08 (s, 1 H), 6.95 – 7.17 (m, 1 H), 2.48 (s, 2 H), 1.38 (s, 9 H).MS (ESI) m/z 276.0 [M+l]+ and 278.2 [M+l]+.

With the rapid development of chemical substances, we look forward to future research findings about 59549-51-8.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-61-4, 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.22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

NBS (0.28g, 1.56mmol) and AIBN (0.05g, 0.31mmol) were added to a solution of Example 52C (0.2g, 1.56mmol)in carbon tetrachloride (10mL) and the mixture was stirred at 80C for 12 hours. Water was added and the aqueouslayer was extracted with dichloromethane. The organic layer was purified by preparative TLC (ethyl acetate) to give thetitle compound (40mg), LCMS (ESI) m/z: 206 [M+1]+.

Statistics shows that 22536-61-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-methylpyrimidine.

Reference:
Patent; Harbin Zhenbao Pharmaceutical Co., Ltd.; Medshine Discovery Inc.; CHEN, Shuhui; CHEN, Zhengxia; DAI, Meibi; XIE, Cheng; LI, Peng; ZHANG, Yang; LIANG, Guibai; WANG, Qiang; LIAO, Jiangpeng; SUN, Fei; HU, Guoping; LI, Jian; (166 pag.)EP3333157; (2018); 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.51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, molecular formula is C7H6Cl2N2O2, molecular weight is 221.0407, as common compound, the synthetic route is as follows.Computed Properties of C7H6Cl2N2O2

Ethyl 2-chloro-4-(4-chloro-3-methoxyphenylamino)pyrimidine-5-carboxylate (RJ1- 061): A mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (0.442 g, 2.0 mmol), 4-chloro-3- methoxyaniline (0.331 g, 2.1 mmol), DIPEA (0.42 mL, 2.4 mmol), and iPrOH (2 mL) was added to a 5 mL microwave vial which was then sealed and placed in a hot oil bath with stirring at 85 C overnight for 17 hours. At this point, a brown solid had formed and this was then washed with iPrOH (10 mL), water (10 mL), iPrOH (10 mL), and hexanes (10 mL) to yield RJ1-061 as a brown solid (0.570 g, 83%). m.p. = 119 C (decomposed). XH NMR (400 MHz, DMSO-) delta 10.27 (s, 1H), 8.81 (s, 1H), 7.48 (d, J= 2.3 Hz, 1H), 7.43 (d, J= 8.6 Hz, 1H), 7.28 (dd, J= 8.6, 2.3 Hz, 1H), 4.37 (q, J= 7.1 Hz, 2H), 3.85 (s, 3H), 1.34 (t, J= 7.1 Hz, 3H). LRMS (ESI+) m/z 342.1 (MC135C135+H)+, 344.0 (MC135C137+H)+, 346.0 (MC137C137+H)+; (ESI-) m/z 339.3 (MC135C135-H)-; HRMS (ESI+) m/z calculated for C14H13CI2N3O3 (M+H)+ 342.04067, found 342.04100.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 20090-58-8, Adding some certain compound to certain chemical reactions, such as: 20090-58-8, name is 4-Chloro-5-methylpyrimidin-2-amine,molecular formula is C5H6ClN3, 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 20090-58-8.

A solution of 4-chloro-5-methylpyrimidin-2-amine (30 mg, 0.20 mmol) in ethanol (0.5 ml) was treated with triethylamine (0.058 ml, 0.41 mmol) and 2,2-dimethyl-3- (methylamino)propan-l-ol (36.7 mg, 0.31 mmol) and the mixture was irradiated in a microwave reactor at 150C for 3.5 h, then quenched with 6N HCl (0.070 ml, 0.41 mmol) and the residue was purified by mass-triggered preparative HPLC (Mobile phase: A = 0.1% TFA/H2O, B = 0.1% TFA/MeCN; Gradient: B = 0 – 30%; 12 min; Column: CI 8) to give 3-((2-amino-5- methylpyrimidin-4-yl)(methyl)amino)-2,2-dimethylpropan-l-ol 2,2,2-trifluoroacetate (6 mg, 0.018 mmol, 8% yield) as a white solid. MS (ES+) C11H20N4O requires: 224, found: 225 [M+H]+. NMR (600 MHz, de-DMSO) delta: 11.95 (brs, 1H), 7.57 (s, 1H), 7.47 (brs, 2H), 4.65 (brs, 1H), 3.71 (brs, 2H), 3.35 (s, 3H), 3.16 (s, 2H), 2.22 (s, 3H), 0.83 (s, 6H).

According to the analysis of related databases, 20090-58-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOARD OF REGENTS, UNIVERSITY OF TEXAS SYSTEM; LEWIS, Richard, Thomas; JONES, Philip; PETROCCHI, Alessia; REYNA, Naphtali; HAMILTON, Matthew, Michael; LEO, Elisabetta; (74 pag.)WO2016/145383; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia