Tag: M.W:200-300

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. 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, molecular formula is C6H4Cl2N2OS, 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. COA of Formula: C6H4Cl2N2OS

After the compound obtained in Step 1 was dissolved in dichloromethane,N, N’-diisopropylamine was added at room temperature, and the reaction mixture was cooled to 0 C and 4,6-dichloro-2- (methylthio) pyrimidine-5-carbaldehyde was added, And stirred for 2 hours.The reaction mixture was extracted with dichloromethane and water.The organic layer was dried over magnesium sulfate and then distilled under reduced pressure.The resulting residue was purified by MPLC to obtain the title compound.

With the rapid development of chemical substances, we look forward to future research findings about 33097-11-9.

Reference:
Patent; Hanrim Pharmaceutical Co., Ltd.; Kim Gyeong-hui; Jin Jeong-uk; Lee Ji-hun; Kim Sin-ae; Jeong Gyeong-jin; Kim Jun-u; Min Sang-hyeon; Ryu Ji-hun; Lee Ju-seok; Lee Won-seok; Song Jae-yeong; Lee Eung-seok; Jeong Tae-cheon; Kim Jeong-ae; (35 pag.)KR2019/73673; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 71406-78-5, 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. 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.

To a stirred solution of (R)-tert-butyl 2-(3-(tert-butoxycarbonyl)piperazin-1-yl)- 7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (12 g, 28.60 mmol, 1.0 equiv) in MeCN (150 mL) was added K2CO3 (7.91 g, 57.20 mmol, 2.0 equiv) and ethyl 4-amino-2- chloropyrimidine-5-carboxylate (6.92 g, 34.32 mmol, 1.2 equiv). The reaction mixture was stirred at 80 C for 12 h, at which point the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification by silica gel chromatography (0%17% EtOAc/petroleum ether) afforded the desired product (16 g, 91.6% yield) as a yellow solid. LCMS (ESI) m/z: [M + H] calcd for C28H40N8O6: 585.32; found 585.1.

According to the analysis of related databases, 71406-78-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REVOLUTION MEDICINES, INC.; SEMKO, Christopher Michael; WANG, Gang; BURNETT, G. Leslie; AGGEN, James Bradley; KISS, Gert; CREGG, James Joseph; GLIEDT, Micah James Evans; PITZEN, Jennifer; LEE, Julie Chu-Li; WON, Walter; THOTTUMKARA, Arun P.; GILL, Adrian Liam; (356 pag.)WO2019/212991; (2019); 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. 38696-21-8, name is 5-Bromo-N,N-dimethylpyrimidin-2-amine, molecular formula is C6H8BrN3, 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. Recommanded Product: 5-Bromo-N,N-dimethylpyrimidin-2-amine

A mixture of 5-bromo-N,N-dimethylpyrimidin-2-amine (99 mg, 0,489 mmol), 1- (3,4-dihydroisoquinolin-2(lH)-yl)-3-(3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenoxy)propan-2-ol (200 mg, 0.489 mmol), Pd(dppf)Cl2 (36 mg, 0.049 mmol), K2C03 (202 mg, 1.47 mmol) in H20-dioxane (1 mL/ 3 mL) was stirred at 100 C with microwave heating for 15 min. The solvent was removed by concentration and the crude product was purified by HPLC separation to give the title compound as the formate salt (76 mg, 38.5%). 1HNMR (CH3OD, 400MHz) delta: 8.59 (s, 2H), 8.35 (br, 1H), 7.42-7.16 (m, 7H), 6.98-6.94 (m, 1H), 4.53-4.46 (m, 3H), 4.18-4.09 (m, 2H), 3.64-3.56 (m, 2H), 3.48-3.39 (m, 2H), 3.26-3.17 (m, 8H). LCMS (m/z): 405.2 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 38696-21-8.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100695; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 56844-40-7, 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. 56844-40-7, name is 6-Bromothieno[2,3-d]pyrimidin-4(3H)-one, molecular formula is C6H3BrN2OS, 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.

Compound 3 (32.7 g, 142 mmol) was mixed with POCl3 (100 mL) and heated at 120 C for 3 h. Then the mixture was quenched into 5 M aq NaOH (1 L) and ice. The pH was adjusted to 7 using a saturated aq NaHCO3 solution. The formed precipitate was isolated by filtration and washed with water (3¡Á200 mL). Drying gave 31.0 g (124 mmol, 88%) of 4 as a brown solid, mp. 112-118 C. A fraction of this material was further purified: the dry material was applied to the top of a packed silica gel plug and eluted with CH2Cl2, mp. 114-118 C; Rf (CH2Cl2/MeOH, 98/2)=0.67; 1H NMR (400 MHz, DMSO-d6) delta: 8.95 (s, 1H), 7.89 (s, 1H); 13C NMR (100 MHz, DMSO-d6) delta: 168.9, 153.2, 152.5, 130.2, 122.9, 118.5; IR (neat, cm-1): 3082, 1508, 1411, 959, 832, 816, 760; HRMS (EI, 70 eV, m/z): 247.8813 (calcd C6H2Br79Cl35N2S, 247.8811, M+). The 1H NMR spectrum corresponds with Ref. 41. 13C NMR spectroscopic data and a reference melting point have not been identified.

According to the analysis of related databases, 56844-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bugge, Steffen; Kaspersen, Svein Jacob; Sundby, Eirik; Hoff, Bard Helge; Tetrahedron; vol. 68; 45; (2012); p. 9226 – 9233;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3438-55-9, 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. 3438-55-9, name is 5-Bromo-4-chloro-6-methylpyrimidine. A new synthetic method of this compound is introduced below.

PREPARATIVE EXAMPLE 6 dl-5-bromo-6-methyl-4-(alpha-methylbenzylamino)pyrimidine (compound number 314) 2.0 g (0.02 mol) of triethylamine and 2.4 g (0.02 mol) of dl-alpha-methylbenzylamine were added to a solution of 4.15 g (0.02 mol) of 5-bromo-4-chloro-6-methyl-pyrimidine in 50 ml of benzene, and the mixture was refluxed with stirring for 5 hours. Upon completion of the reaction, the reaction product was washed with water, dried over anhydrous sodium sulphate and the benzene was distilled off to leave an oil. This oil was then caused to crystallize using column chromatography (Wakogel C-200, eluted with a 1:1 mixture of benzene and ethyl acetate). Crystals were obtained and recrystallized from n-hexane to give 2.6 g of the desired product in the form of pale yellow prisms melting at 85-87 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-55-9, its application will become more common.

Reference:
Patent; Sankyo Company, Limited; Ube Industries, Limited; US4435402; (1984); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 6299-85-0, 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. 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

EXAMPLE 8 Preparation of (S)-6-((l -amino- 1 -oxopropan-2-yl)amino)-2-(4-(4- (trifluoromethyl)phenoxy)phenyl)pyrimidine-4-carboxamide (Cpd No. 14) Scheme 17 (S)-methyl 2-chloro-6-((l -methoxy- 1 -oxopropan-2-yl)amino)pyrimidine-4- carboxylate: To a mixture of methyl 2,6-dichloropyrimidine-4-carboxylate (5.175 g, 25.00 mmol) in acetonitrile (100 mL) was added (S)-methyl 2-aminopropanoate hydrochloride (3.497 g, 25.05 mmol) and iPr2NEt (9.6 mL, 55.1 mmol). The mixture was heated at 50C overnight then concentrated in vacuo. The residue was chromatographed over silica gel with 30-70% EtOAc in hexanes. The product fractions were evaporated in vacuo to yield (S)-methyl 2-chloro-6-((l-methoxy-l – oxopropan-2-yl)amino)pyrimidine-4-carboxylate as a thick yellow-orange oil (4.194 g, 15.33 mmol, 61% yield). LC/MS: m/z= 274.2 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PURDUE PHARMA L.P.; NI, Chiyou; PARK, Minnie; SHAO, Bin; TAFESSE, Laykea; YAO, Jiangchao; YOUNGMAN, Mark; WO2013/30665; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 130049-82-0, 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.130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, molecular formula is C11H15ClN2O2, molecular weight is 242.7, as common compound, the synthetic route is as follows.

A solution of oxalylchloride (8.8 ml) in dichloromethane (20 ml) was cooled to -65C and a solution of dimethyl sulfoxide (6.5 ml) dissolved in dichloromethane (20 ml) was added to it slowly and stirred for 30 min. keeping the temperature at -650C a solution of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[l,2-a]pyrimidin-4-one (5 grams) (formula-7) dissolved in dichloromethane (30 ml) was added to it very slowly and stirred for 40 min. Triethyl amine was added to the reaction mixture and then quenched with water. The organic layer was separated, washed with aqueous sodium carbonate and water. The solvent from the organic layer was distilled off under reduced pressure to provide the title compound. Yield: 4.0 grams

The chemical industry reduces the impact on the environment during synthesis 130049-82-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; ESWARAIAH, Sajja; SATYANARAYANA, Revu; WO2010/4578; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 16234-14-3, 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 16234-14-3 as follows.

2-Chlorothieno[3,2- Pd/C (8.90 mg, 20%> by wt) was added after 12 h. The reaction mixture was filtered through Celite with EtOAc washings. The filtrate was washed with H20/brine (4:1), dried (MgS04), and concentrated under reduced pressure to provide 16 (33.0 mg, 90%) as white solid: Mp 164.9-165.5 C (EtOAc); IR (ATR, neat) 3105, 3051, 2924, 1543, 1515, 1456, 1420, 1334, 1349, 1301, 1159, 794 cm”1; 1H NMR (DMSC fe 300 MHz) delta 9.50 (s, 1 H), 8.64 (d, 1 H, J= 5.4 Hz), 7.64 (d, 1 H, J= 5.4 Hz); 13C NMR (DMSO-d6, 75 MHz) delta 162.7, 156.3, 155.3, 142.2, 130.1, 122.9; MS (EI) m/z 170 (M+, 100), 135 (72);HRMS (EI) m/z calcd for C6H3N2SC1 169.9705, found 169.9700.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16234-14-3, its application will become more common.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; WIPF, Peter; WANG, Qiming, Jan; WO2012/78859; (2012); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 10244-24-3 , The common heterocyclic compound, 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, molecular formula is C12H17ClN4O2, 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.

Example 4 Preparation of Buparlisib (0036) Added compound 6 (14.4 g, 0.06 mol), bis(pinacolato)diboron (compound 5) (18.2 g, 0.072 mol), DMSO (200 mL), KOAc (17.64 g, 0.18 mol) and PdCl2(PPh3)2 (4.2 g, 0.006 mol) into a second reactor, then heated the resulting mixture to 5 C. and kept the reaction for 7 hours, and then added compound 4 (17 g, 0.06 mol) into the second reactor, kept the reaction for 16 hours. Put the reaction solution into water after the reaction was finished, and large amount of solid were separated. The resulting mixture was filtered, stirred with methanol/acetone (V:V=1:1) and crystallized for 3 hours. The filter cake was dried in vacuo at 60 C. for 8 hours to obtain the buparlisib product (compound 1) as a white solid (23.15 g, yield 94%), HPLC purity: 99.2%. Mass Spectrum: M+H- 411.

The synthetic route of 10244-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XU, YONG; (6 pag.)US2016/264546; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 33097-13-1 ,Some common heterocyclic compound, 33097-13-1, molecular formula is C6H3Cl2N3S, 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.

[0408] Step 1 : To a suspension of 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (176 mg, 0.8 mmol) in DMF (2 mL) was added benzo[d][l,3]dioxol-5-amine (137.1 mg, 1 mmol). After stirring at room temperature for 15 h, the mixture was diluted with water, the resulting precipitate was collected by filtration to give 4-(benzo[d][2,3]dioxol-5-ylamino)-6- chloro-2-(methylthio)pyrimidin-5-carbonitrile (273 mg).

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. 33097-13-1, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; XU, Qing; HUANG, Wolin; JIA, Zhaozhong J.; SONG, Yonghong; WO2012/61415; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia