Tag: M.W:200-300

Reference of 187035-79-6, 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 187035-79-6 as follows.

To a solution of (R)-methyl l-isopropyl-7-(methylsulfonyl)-l,2,3,4- tetrahydrobenzo[4,5]imidazo[l,2-a]pyrazine-8-carboxylate (80 mg, 0.228 mmol) in ‘PrOH (2 mL) and DCM (1 mL) was added ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate (174 mg, 0.684 mmol) and DIEA (177 mg, 1.37 mmol). The mixture was stirred at 60 C overnight. Water (5 mL) was added to the mixture and the aqueous layer was extracted with EtOAc (2 X 10 mL). The combined organic layers were washed with water (2 X 10 mL) and brine, dried over anhydrous Na2S04, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford (R)-methyl 2-(5-(ethoxycarbonyl)-4- (trifluoromethyl)pyrimidin-2-yl)-l-isopropyl-7-(methylsulfonyl)- 1,2,3,4- tetrahydrobenzo[4,5]imidazo[l,2-a]pyrazine-8-carboxylate (75 mg, 57.8% yield) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,187035-79-6, its application will become more common.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; GREGG, Richard, E.; (143 pag.)WO2015/195922; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 32980-71-5, 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.32980-71-5, name is Perchloropyrimido[5,4-d]pyrimidine, molecular formula is C6Cl4N4, molecular weight is 269.9, as common compound, the synthetic route is as follows.

Connect a mineral oil valve rotating device, an impregnation thermometer, to a 4-cc bottle with a capacity of 100 cc.a vent and a drying tube, Add 7g piperidine and 30cc absolute ethanol to the bottle. Then, 2.7 g of tetrachloropyrimidopyrimidine was added with stirring. Increasing the reaction temperature to 32-35 C produces a moderate amount of basic steam. The powder reaction gradually changes from a yellow-gold-red crystal powder to a transparent granular powder.The tetrachloro compound is gradually added in 30 minutes. The reaction mixture was continuously stirred for 90 minutes and then allowed to stand for 24 hours. After the reaction was completed, it was observed that there was a bright yellow powder in the bright orange liquid, and the color of the liquid became more vivid when it was left standing. The precipitate was collected by filtration and washed with absolute ethanol to give 3.24 g of a yellow powder of unknown melting point which softened at 180 C and rapidly melted and decomposed at 240 C.The yellow powder was purified by adding 30 cc of dimethylformamide precooled at 0 C, and the dimethylformamide was turned into a deep red color. The precipitate was collected by suction filtration using a vacuum suction apparatus, and the residual dimethyl group was removed by washing with 10 cc of absolute ethanol. Formamide,The weight of the product is less than half the weight of the original material.The melting point is raised to 245 ~ 255 C, And softening occurs at 225 C. The average yield of the two chlorination reactions and subsequent reaction with piperidine is from 27 to 29%, based on the piperidine derivative, wherein the oxidized uric acid used in the chlorination reaction stage is in the form of its dried disodium salt.

Statistics shows that 32980-71-5 is playing an increasingly important role. we look forward to future research findings about Perchloropyrimido[5,4-d]pyrimidine.

Reference:
Patent; Suohao; Huan Xiaojun; Suo Hao; Qi Taotao; Jin Chunyan; Chen Yifei; (9 pag.)CN108752350; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 74901-69-2, 2,4-Dichloro-6,7-dihydrothieno[3,2-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, Quality Control of 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine, blongs to pyrimidines compound. Quality Control of 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

Example 1 1.1 (2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)-(3-fluorophenyl)-amine (III-1) 4 g (II) are placed in 15 ml dimethylformamide, then 4.5 ml diisopropylethylamine and then 2.5 ml 3-fluorophenylamine are added. The reaction mixture is heated to 120 C., until no further reaction takes place, then cooled and evaporated down. The residue is mixed with water. The product is extracted with dichloromethane and purified by chromatography (silica gel, petroleum ether/ethyl acetate 80/20 to 60/40). 2.6 g (III-1) are obtained as a solid. Analytical HPLC (method A): RT=3.27 min.

The synthetic route of 74901-69-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/305102; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
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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 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. name: 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

To a stirred reaction mixture of 3-(6-methylpyridin-2-yl)-1-(4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)phenyl)pyrrolidin-2-one was added 5-bromo-7-methyl-7/-/-pyrrolo[2,3- d]pyrimidin-4-amine (0.479 g, 2.1 mmol, 1.0 equiv) of and 8 ml of sat. NaHC03 solution under argon atmosphere, followed by addition of PdCl2(dppf)-CH2Cl2 adduct (0.086 g, 0.11 mmol, 0.05 equiv) under argon atmosphere, the reaction mixture was heated to 100 C and stirred for overnight. Reaction mixture was monitored by LCMS and after consumption of starting material, Reaction mixture was filtered through celite and washed with DCM. The filtrate was and dried over Na2S04 and concentrated to get crude product. Crude product was purified by flash chromatography on Silica gel and compound was eluted with 2% MeOH/DCM as impure fraction, it was re purified by prep HPLC(Column :Column : Inertsil ODS 3V (250 mm X 4.6 mm X 5 mic), Mobile phase (A) : 0.01 % Ammonia in water, Mobile phase(B) : ACN, Flow rate : 1.0 mL/min) to get 1-4-(4-amino-7- methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl)-3-(6-methylpyridin-2-yl)pyrrolidin-2-one as off-white solid, yield (0.07g, 10%). LCMS (ES) m/z = 399.2 [M+H]+. H NMR (400 MHz, DMSOd6) delta 2.44 (s, 3 H), 2.49 – 2.53 (m, 2 H), 3.73 (s, 3 H), 3.92 – 4.07 (m, 3 H), 6.03 (br s, 2 H), 7.13 – 7.20 (m, 2 H), 7.29 (s, 1 H), 7.46 (d, J=8.4 Hz, 2 H), 7.65 (t, J=7.6 Hz, 1 H), 7.79 (d, J=8.4 Hz, 2 H), 8.14 (s, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 1337532-51-0.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey M.; MEDINA, Jesus Raul; WO2015/136463; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1337532-51-0, 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. 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C7H7BrN4, 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 stirred solution of 1-(4-bromophenyl)-3-(2,6-dimethylpyrimidin-4-yl)pyrrolidin-2-one (0.6 g, 1.734 mmol, 1.0 equiv), was added bis(pinacolato)diboron (0.441 g, 1.7 mmol, 1.0 equiv), and potassium acetate (0.510 g, 5.2 mmol, 3.0 equiv), and the mixture was degassed with Argon for 10 minutes, PdCI2(dppf)-CH2CI2 adduct (0.071 g, 0.09 mmol, 0.05 equiv) was added and again degassed with Argon for 10 minutes. The reaction mixture was stirred for 3 hours at 100 C in a sealed vessel. The reaction was cooled to room temperature. 5-bromo-7-methyl-7/-/-pyrrolo[2,3-c]pyrimidin-4-amine (0.394 g, 1.734 mmol, 1.0 equiv) and saturated aqueous NaHC03 (6 mL) were added, and Argon gas was bubbled through the mixture for 10 minutes. PdCl2(dppf)-CH2Cl2 adduct (0.071 g, 0.09 mmol, 0.05 equiv) was added, the vessel was sealed, and the reaction mixture was stirred overnight at 100 C. The crude mixture was filtered through celite and the filtrate was dried over Na2S04 and concentrated. Purification: Crude material was purified by flash column chromatography using silica gel column, compound was eluted at 8-10 % MeOH :DCM as mobile phase.yield: (0.055 g, 7.7 %) as off white solid. LCMS (ES) m/z = 414.2 [M+H]+. H NMR (400 MHz, CDCI3) delta 2.50 (s, 3 H), 2.57 – 2.61 (m, 1 H), 2.67 (s, 3 H), 2.71 – 2.78 (m, 1 H), 3.84 (s, 3 H), 3.91 – 4.00 (m, 2 H), 4.09 – 4.15 (m, 1 H), 5.23 (br s, 2 H), 6.94 (s, 1 H), 7.13 (s, 1 H), 7.49 (d, J=8.40 Hz, 2 H), 7.76 (d, J=8.0 Hz, 2 H), 8.33 (s, 1 H).

According to the analysis of related databases, 1337532-51-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey M.; MEDINA, Jesus Raul; WO2015/136463; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 108381-28-8, Adding some certain compound to certain chemical reactions, such as: 108381-28-8, name is 4-(Benzyloxy)-2-chloropyrimidine,molecular formula is C11H9ClN2O, 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 108381-28-8.

Step 1-Synthesis of (S)-4-(benzyloxy)-N-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)phenyl)pyrimidin-2-amine (cb): (S)-4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)aniline (ca) (68.6 mg1.00 equiv, 210.17 mumoles) was weighed into a microwave vial with a stirbar. 4-(benzyloxy)-2-chloropyrimidine (57.4 mg, 1.24 equiv, 260.13 mumoles), sodium t-butoxide (31.4 mg, 326.73 mmoles), bis(dibenzylideneacetone)palladium (8.6 mg14.96 mumoles) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (7.3 mg18.55 mumoles) were added, then the reaction vial was evacuated and purged with N2 3 times. Toluene (2 mL) was added, and the reaction was heated in a CEM microwave at 120 C. for 40 minutes with PowerMax off. The reaction was then filtered through Celite, washing with CH2Cl2. The crude material was concentrated under reduced pressure onto silica gel, and was then purified using flash chromatography on a 4 g column using a gradient of 0% to 100% EtOAc in heptane. The product containing fractions were concentrated to give (S)-4-(benzyloxy)-N-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)phenyl)pyrimidin-2-amine (cb) (77 mg0.72 equiv150.80 mumoles71.75% yield) as an oil. 1H NMR (400 MHz, CDCl3) delta 8.40-8.33 (m, 2H), 8.18 (d, J=5.7, 1H), 7.66 (d, J=8.8, 2H), 7.49-7.30 (m, 5H), 6.28 (d, J=5.7, 1H), 5.44 (s, 2H), 4.48-4.29 (m, 2H), 4.09-3.45 (m, 6H), 2.72-2.49 (m, 2H), 2.03-1.91 (m, 2H), 1.72-1.50 (m, 2H), 1.34 (d, J=6.7, 3H).

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. 108381-28-8, 4-(Benzyloxy)-2-chloropyrimidine, other downstream synthetic routes, hurry up and to see.

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

Synthetic Route of 1004524-64-4, 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 1004524-64-4 as follows.

Example 3: N-[4-(4-Aminopyrimidin-2-yloymethyl)-benzyl]-tetramethylrhodamine-6-carboxamide (3) and N-[4-(4-Aminopyrimidin-2-yloxymethyl)-benzyl]-tetramethylrhodamine-5-carboxamide (4) [Show Image] 2-(4-(Aminomethyl)benzyloxy)pyrimidin-4-amine (2) (3.6 mg, 0.016 mmol) and 5(6)-carboxytetramethylrhodamine succinimidyl ester (8.2 mg, 0.016 mmol) are dissolved in 800 muL DMF with 2.4 muL TEA and heated overnight at 31 C. The solvent is evaporated in vacuo and the compounds are isolated by reversed phase MPLC (medium pressure liquid chromatography) on a C18 column using a linear gradient of water:acetonitrile (from 95:5 to 20:80 in 20 min, 0.08% TFA). MS (ESI) m/z 643 [M-CI]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1004524-64-4, its application will become more common.

Reference:
Patent; EPFL Ecole Polytechnique Federale de Lausanne; EP1882688; (2008); 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. 71406-78-5, name is Ethyl 4-amino-2-chloropyrimidine-5-carboxylate, molecular formula is C7H8ClN3O2, 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. SDS of cas: 71406-78-5

LiOH (238 g, 9.94 mmol) was added to a solution of commercially available ethyl 4- amino-2-chloro-pyrimidine-5-carboxylate (1 g, 4.96 mmol) in THF (20 ml_) and water (20 ml_) and the mixture stirred at room temperature for 30 mins. The volatile solvent was removed in vacuo and the remaining aqueous solution was washed with Et20 (20 ml_). The aqueous portion was acidified with 2M HCI and the resulting white precipitate was collected by filtration, washed with water and dried in vacuo to afford the titled compound as a white solid. (1359) LC-MS (Method 3A): Rt 1.00 mins; MS m/z 174.0 = [M+H]+ (1360) 1 H NMR (500 MHz, DMSO-d6) d 13.55 (s, 1 H), 8.58 (s, 1 H), 8.47 (s, 1 H), 7.98 (s, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 71406-78-5.

Reference:
Patent; ADORX THERAPEUTICS LIMITED; MCCARTHY, Clive; MACLEOD, Calum; MOULTON, Ben; LENAGH-SNOW, Gabriel; (190 pag.)WO2019/122932; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 63931-21-5, Adding some certain compound to certain chemical reactions, such as: 63931-21-5, name is 5-Bromo-2,4,6-trichloropyrimidine,molecular formula is C4BrCl3N2, 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 63931-21-5.

5-Bromo-2,4,6-trichloropyrimidine (1.30 g, 4.96 mmol) and 3-(trifluoromethyl)- bicyclo[l.l. l]pentan-l- amine hydrochloride (985 mg, 4.99 mmol) were suspended in acetonitrile (6.5 mL) and N,N-diisopropylethylamine (1.55 g, 2.1 mL, 12 mmol) was added at room temperature. The resulting yellow solution was stirred for 7 h at room temperature. After that, the reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 80 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 10:90) to yield, after drying in vacuo (40C, 5 mbar), the title compound as an off-white solid (1.487 g, 80%). HPLC (method LCMS_fastgradient) tR = 1.50 min. 1H NMR (CDC13, 300 MHz): delta 2.46 (s, 6 H), 6.10 (br s, 1 H). MS (ES+) m/z 375.9, 377.9, 379.8 [M+H, Br & 2 CI isotopes].

According to the analysis of related databases, 63931-21-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; JAKOB-ROETNE, Roland; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; STEINER, Sandra; (89 pag.)WO2018/11164; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 2915-16-4, Adding some certain compound to certain chemical reactions, such as: 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine,molecular formula is C16H11ClN2, 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 2915-16-4.

Inthe nitrogen ambient, after the compound 1-3 20 g (46.5 mmol) was melted in thetetrakis tetrahydrofuran (THF) 0.2 L here 2- chloro- 4,6- diphenylpyrimidine (2-chloro-4,6-diphenylpyrimidine)12.4 g (46.5 mmol) and tetrakis (triphenylphosphine) palladium(tetrakis(triphenylphosphine)palladium) 0.54 g (0.47 mmol) were put and itmixed. The saturated potassium carbonate 16.1 g (116 mmol) was put in water andit heated up in 80 for 15 hours and it refluxed.After water was put in into the reaction solution after the reaction completionand it extractedin the dichloromethane (DCM) moisture was removed to the anhydrous MgSO4 itfiltered and it was concentrated under reduced pressure. The residue obtainedin this way was refined to the flash column chromatography after dividing andthe compound A -14 20.4 g (82 %) was obtained.

According to the analysis of related databases, 2915-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cheil Industries Co., Ltd.; Oh, Jae Jin; Kang, Gi Wook; Kang, Uii Soo; Kim, Yun Hwan; Kim, Hun; Yang, Yong Tak; Yu, Uhn Sun; Lee, Nam Hun; Lee, Han Ir; Jo, Pyung Suk; (66 pag.)KR2015/28579; (2015); A;,
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Pyrimidine – Wikipedia