Tag: M.W:200-300

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. 31169-25-2, name is 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 31169-25-2

Dimethylformamide (25.8 mL, 0.33 mol) and dichloromethane (150 mL) were added to a reactor. Oxalyl chloride (46.4 mL, 0.53 mol) diluted with dichloromethane (150 mL) at room temperature was added to the reactor for about 30 minutes. 7-bromothieno[3,2- d]pyrimidin-4(3H)-one (35 g, 0.15 mol) was added thereto, and then, the reaction solution was heated to reflux for 3 hours. The temperature of the reaction solution was lowered and water was carefully added thereto. The organic layer was separated, and the aqueous layer was subjected to extraction using dichloromethane. The extracted organic layer was dried over anhydrous sodium sulfate. The dried organic layer was filtered and distilled under reduced pressure, and dried with nitrogen gas to obtain the title compound (30.5 g, 85percent). 1H-NMR Spectrum (300 MHz, DMSO-: delta 9.16 (s, 1H), 8.79 (s, 1H)

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, 31169-25-2, 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one.

Reference:
Patent; HANMI PHARM CO., LTD.; BAE, In Hwan; SON, Jung Beom; HAN, Sang Mi; KWAK, Eun Joo; KIM, Ho Seok; SONG, Ji Young; BYUN, Eun Young; JUN, Seung Ah; AHN, Young Gil; SUH, Kwee Hyun; WO2013/100632; (2013); 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. 90914-41-3, name is 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

To a stirred solution of 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (3.5 g, 15.02 mmol, 1 equiv) in DMF (60 mL) was added sodium hydride (0.72 g, 18.02 mmol, 1.2 equiv) at 0C. The reaction mixture was stirred for 15 mm at 0C. Methyl iodide (1.12 mL, 18.02 mmol, 1.2 equiv) was added to the reaction mixture at 0C. The reaction mixture was warmed to room temperature and stirred for 3h. The reaction mixture was quenched with ice water and extracted in ethyl acetate. The organic layer was dried over sodium sulphate and evaporated to obtain crude product, which was purified over silica gel flash column chromatography. The compound eluted out in 30% EtOAc in n-Hexane. Fractions obtained were concentrated to give 3-bromo-4-chloro- 1-methyl-i H-pyrazolo[3,4- d]pyrimidine (2.0 g, 57%) as pale yellow solid. LCMS (ES) m/z = 247.4, 249.4 [M+H. ]. 1H NMR (400 MHz, DMSO-d6) O ppm -4.03 (5, 3H), 8.88 (5, 1H)

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, 90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; (110 pag.)WO2017/46738; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 852180-74-6, Adding some certain compound to certain chemical reactions, such as: 852180-74-6, name is 3-(Pyrimidin-5-yl)benzoic acid,molecular formula is C11H8N2O2, 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 852180-74-6.

A mixture of 3-pyrimidin-5-yl-benzoic acid (100 mg, 0.50 mmol) and SOCl2 (73 mu, 1.0 mmol) was heated under reflux for 4 h. The solvent was evaporated off under reduced pressure and the residue was dissolved in DCM (5 mL) and slowly added to a mixture of 4- (chlorodifluoromethoxy)aniline (106 mg, 0.55 mmol) and TEA (140 mu, 1.0 mmol) in DCM (5 mL). The mixture was stirred at RT overnight. The solvent was evaporated off under reduced pressure and the residue was suspended in EtOAc (10 mL),filtered through a 10 muetaiota Isolute fritted cartridge and the filtrate was evaporated to dryness under reduced pressure to give the crude product which was purified by preparative HPLC to afford the title compound. LC-MS (Condition 4) tR = 1.15 min, m/z = 375.8 [M+H]+; XH-NMR (400 MHz, DMSO-d6) delta ppm 7.40 (d, J = 9.05 Hz, 2 H) 7.73 (t, J = 7.82 Hz, 1 H) 7.92 (m, 2 H) 8.06 (t, J = 6.97 Hz, 2 H) 8.37 (t, J = 1.96 Hz, 1 H) 9.24 – 9.29 (m, 3 H) 10.52 (s, 1 H).

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. 852180-74-6, 3-(Pyrimidin-5-yl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GROTZFELD, Robert Martin; JONES, Darryl Brynley; MANLEY, Paul; MARZINZIK, Andreas; MOUSSAOUI, Saliha; PELLE, Xavier Francois Andre; SALEM, Bahaa; SCHOEPFER, Joseph; WO2013/171641; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13479-88-4 , The common heterocyclic compound, 13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, 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.

[00492] (+/-)-trans-Methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (284 mg, 1.55 mmol)and 5,7-dichlorothiazolo[5,4-d]pyrimidine (352 mg, 1.71 mmol) were dissolved in DMF (5 mL), then potassium carbonate (428 mg, 3.10 mmol) was added. The mixture was stirred at rt overnight. The reaction was stopped, and to the reaction mixture was added water (50 mL). The resulting mixture was extracted with ethyl acetate (50 mL x 2). The combined organic layers were washed with saturated brine (80 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to remove the solvent and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 10/1) to give the title compound as a yellow solid (317 mg, 58%).MS (ESI, pos.ion) m/z: 353.0 [M+H]1H NMR (600 MHz, CDC13) (ppm): 8.75 (s, 1H), 6.49 (d, J = 4.7 Hz, 1H), 4.63 (s, 1H), 3.76 (s, 3H), 2.50 (d, J= 5.6 Hz, 1H), 2.01 (d, J= 1.8 Hz, 1H), 1.95 (d, J= 2.5 Hz, 1H), 1.88- 1.76 (m, 2H), 1.73- 1.53 (m, 6H).

The synthetic route of 13479-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 148550-51-0, 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. 148550-51-0, name is Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate, molecular formula is C8H10N2O4S, 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.

A solution of 2-methanesulfonyl-pyrimidine-5-carboxylic acid ethyl ester (0.0434 mol) in acetonitrile is added under nitrogen to a solution of 4-N-(tertbutoxycarbonyl) aminopiperidine (0.0362 mol) and potassium carbonate (0.0724 mol). The mixture was stirred at room temperature for 15 hours, poured out onto ice. The precipitate was filtered, washed with water and DIPE and dried yielding 7.9g of intermediate 4.

According to the analysis of related databases, 148550-51-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/122926; (2006); 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. 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, the common compound, a new synthetic route is introduced below. name: 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde

To the solution of phosphorus oxy chloride (65 mL, 0.70 mol) in trichloroethylene (46.5 mL) was added DMF (25 mL, 0.32 mol) slowly to keep the temperature between 5 0C to 10 0C. The solution was then warmed up to room temperature before 6-hydroxy-2-(methylthio)-4(lH)- pyrimidinone (25 g, 0.16 mol) was added in portions. The resultant reaction mixture was heated at 80 0C overnight followed by concentration under vacuum. The resulting slurry like residue was poured into ice, stirred for 2 hours then filtered to afford the crude product. The crude product was further purified by recrystalization with hexane to afford 4,6-dichloro-2-(methylthio)-5- pyrimidinecarbaldehyde (21.3 g , 61%). 1H-NMR (CDCl3) delta 2.66 (s, 3 eta), 10.4 (s, 1 eta).To a solution of 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde (10.0 g, 44.8 mmol) in TetaF (250 mL) was added 2,6-difluoroaniline (5.35 mL, 49.3 mmol, 1.1 eq) followed by Et3N (12.6 mL, 89.6 mmol, 2 eq). The reaction mixture was heated to 550C for about 22 h before concentrated. The slurry was re-dissolved in DCM (250 mL) and washed with H2O (2 x 100 mL), then concentrated and further washed with acetone (2 x 10 mL) to give 9.87 g (70 %) of pure 4- chloro-6-[(2,6-difluorophenyl)amino]-2-(methylthio)-5-pyrimidinecarbaldehyde. LC-MS m/z 316 (M+H)+.A solution of 4-chloro-6-[(2,6-difluorophenyl)amino]-2-(methylthio)-5- pyrimidinecarbaldehyde (200 mg, 0.63 mmol) in DMF (4.0 mL) and acetic anhydride (2.0 mL) was heated with a microwave (16O0C) for about 30 minutes. The resultant mixture was then concentrated. Flash chromatography (EtOAc / Hexane, 1 : 5) provided the title compound (109 mg, 51%): LC-MS m/z 340 (M+H)+.

The synthetic route of 33097-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/147103; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 98141-42-5, 4,6-Dichloro-1-methyl-1H-pyrazolo[3,4-d]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: 4,6-Dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. name: 4,6-Dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

To a stirred solution of (rac)-(2S,4R,6S,7S)-methyl 7-aminotricyclo[3.2.2.02,4]nonane-6-carboxylate (3.4 g, 17.4 mmol) in THF (150 ml) was added 4,6-dichloro-1-methyi-1Hpyrazolo[3,4-d]pyrimidine (4.24 g, 20.9 mmol) and (3.38 g, 4.52 ml, 26.1 mmol) at roomtemperature and the resulting reaction mixture solution was stirred at 60 oc for 16 h. After cooling to room temperature, the reaction mixture was poured into water (1 00 ml) andextracted with EtOAc (150 ml twice). The combined organic layers were washed with brine,dried over anhydrous Na2S04 , filtered and concentrated in vacuo to give a crude product,which was purified by silica gel flash chromatography (0-1 00% EtOAc-hexane gradient) toafford the title racemic compound (4.1 g, 65.1% yield) as a white solid. MS: 362.0 [M+Ht.

The synthetic route of 98141-42-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; TAN, Xuefei; ZBINDEN, Katrin Groebke; KUHN, Bernd; WANG, Lisha; LIU, Yongfu; WU, Jun; SHEN, Hong; SHI, Tianlai; (174 pag.)WO2017/133664; (2017); 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. 876343-10-1, name is 4-Chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H3ClIN3

4-(3-Hydroxypropyl)benzeneboronic acid (2.51 1 g, 13.95 mmol) and 4-chloro-6-iodo-7H- pyrrolo[2,3-d]pyrimidine (3.44 g, 12.31 mmol) were dissolved in 1 -propanol (100 ml) at RT and an aq. solution of Na2CC>3(2 M) (13.54 ml, 27.1 mmol) was added. Argon was bubbled through the mixture for 5 min and PdCI2(PPh3)2(0.432 g, 0.615 mmol) was added. The RM was stirred at 105C for 22 h and then allowed to cool to RT overnight. The solvent was removed and the residue was sonicated in a mixture of water and THF (3:2). The mixture was filtered, the solids were washed with water and dried to afford the title compound as a solid (2.4 g). Method A: Rt = 0.86 min; [M+H]+= 288.2

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, 876343-10-1, 4-Chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; NOVARTIS AG; ARISTA, Luca; HEBACH, Christina; HOLLINGWORTH, Gregory John; HOLZER, Philipp; IMBACH-WEESE, Patricia; LORBER, Julien; MACHAUER, Rainer; SCHMIEDEBERG, Niko; VULPETTI, Anna; ZOLLER, Thomas; (178 pag.)WO2019/186343; (2019); 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. 56686-16-9, name is 5-Bromo-2,4-dimethoxypyrimidine. A new synthetic method of this compound is introduced below., SDS of cas: 56686-16-9

5-Bromo-2,4-dimethoxypyrimidine (0.29 g, 1.3 mmol) in anhydrous THF was added dropwise to a 2.93mol/L n-BuLi/hexane solution (0.47 mL, 1.4 mmol ) at 195 K under an argon atmosphere. After 30 min, 6a (0.52 g, 1.3 mmol) was slowly added to the reaction mixture at 195 K and stirred for 1 h at 195 K. The reaction was quenched with 20 mL water. The mixture was warmed to room temperature and extracted with ether. The organic layer was dried over MgSO4, filtrated and evaporated. The crude product was purified by column chromatography on silica gel using the mixture of petroleum ether and ethyl acetate (v/v = 6/1) as the eluent to give 1o (0.35 g, 52%) as a colorless solid. Mp 367-368 K; Calcd for C23H18F6N2O3S (%): Calcd C, 53.49; H, 3.51; N, 5.42. Found C, 53.53; H, 3.54; N, 5.47; 1H NMR (400 MHz, CDCl3, ppm): delta 2.01 (s, 3 H, -CH3), 3.74 (s, 3H, -OCH3), 3.84 (s, 3H, -OCH3), 4.01 (s, 3H, -OCH3), 6.91 (d, 2H, J = 8.0 Hz, benzene-H), 7.06 (s, 1H, thiophene-H), 7.45 (d, 2H, J = 8.0 Hz, benzene-H), 8.33 (s, 1H, pyrimidine-H); 13C NMR(100 MHz, CDCl3, ppm): delta 14.08, 54.16, 55.21, 55.30, 104.13, 114.36, 121.38, 125.91, 126.16, 126.84, 138.58, 142.05, 159.04, 159.47, 166.05, 168.03; IR(KBr, n, cm-1): 507, 544, 650, 739, 758, 799, 822, 841, 891, 986, 1003, 1034, 1074, 1123, 1198, 1257, 1298, 1337, 1371, 1408, 1476, 1518, 1549, 1595, 1647, 2843, 2941, 2964, 3014, 3412, 3688; LRMS, ESI+ m/z 517.1 (MH+, [C23H19F6N2O3S]+ requires 517.1).

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, 56686-16-9, 5-Bromo-2,4-dimethoxypyrimidine.

Reference:
Article; Liu, Hongliang; Pu, Shouzhi; Liu, Gang; Chen, Bing; Tetrahedron Letters; vol. 54; 7; (2013); p. 646 – 650;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1260088-72-9, 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]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, Application In Synthesis of 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine

Step 4-Synthesis of q: To a cool (0 C.) solution of 2,4-dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine (p) (2.53 g, 11.5 mmol), DIPEA (4.8 mL, 28 mmol) and DMF (15 mL) was added (3S)-3-methylmorpholine (1.42 g, 14 mmol), the solution was allowed to warm slowly over 15 h. The solution was poured into sat. NH4Cl (100 mL) and extracted with ether (3×50 mL). The combined org. phases were washed with brine (1×25 mL), dried (MgSO4), filtered, and concentrated to afford 3.18 g (95%) of (S)-2-chloro-7,7-dimethyl-4-(3-methylmorpholino)-5,7-dihydrofuro[3,4-d]pyrimidine (q) as a colorless solid: 1H NMR (400 MHz, CDCl3) delta 5.10 (d, J=11.3 Hz, 1H), 5.05 (d, J=11.3 Hz, 1H), 4.11 (s, 1H), 3.85-4.00 (m, 2H), 3.84-3.66 (m, 2H), 3.55 (ddd, J=11.9, 11.9, 2.8 Hz, 1H), 3.39 (ddd, J=13.0, 13.0, 3.2 Hz, 1H), 1.47 (s, 3H), 1.46 (s, 3H), 1.36 (d, J=6.8 Hz, 3H); LC-MS: m/z=+284 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1260088-72-9, 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; US2010/331305; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia