Tag: M.W:100-200

Application of 5018-38-2, 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. 5018-38-2, name is 4,6-Dichloro-5-methoxypyrimidine, molecular formula is C5H4Cl2N2O, 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.

Example 3: Preparation of 6-chloro-N-[2-[2-fluoro-4-[[4-(trifluoromethyl)-2-pyridyl] oxy]phenyl]ethyl]-5-methoxy-pyrimidin-4-amine (V-14) To a solution of 2-[2-fluoro-4-[[4-(trifluoromethyl)-2-pyridyl]oxy]phenyl]ethanamine hydrochloride (344 mg, 0.9 mmol) in NMP (5 ml.) was added diisopropylethylamine (0.36 mL, 2.1 mmol). The solution was stirred for 5 min at room temperature at which time 4,6-dichloro-5-methoxypyrimidine (150 mg, 0.8 mmol) was added. The reaction mixture was stirred at 80C overnight then allowed to cool to room temperature. Water was added and was extracted with MTBE (3x). The combined organic layers were washed with water, dried over Na2S04, and concentrated in vacuo. The residue was purified by flash silica column chromatography to provide 288 mg (0.65 mmol, 78%) of the light yellow oily product.

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 5018-38-2, 4,6-Dichloro-5-methoxypyrimidine.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; GRAMMENOS, Wassilios; CRAIG, Ian, Robert; BOUDET, Nadege; MUeLLER, Bernd; DIETZ, Jochen; LAUTERWASSER, Erica, May, Wilson; LOHMANN, Jan, Klaas; MONTAG, Jurith; WO2013/113720; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 308348-93-8, 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.308348-93-8, name is Methyl 2-aminopyrimidine-5-carboxylate, molecular formula is C6H7N3O2, molecular weight is 153.14, as common compound, the synthetic route is as follows.

Methyl 2-aminopyrimidine-5-carboxylate (300 mg, 2.0 mmol) was diluted in methanol (5 ml_) containing a few drops of water. Lithium hydroxide (122 mg, 5.1 mmol) was added, and the reaction mixture was stirred at 60 0C overnight. The mixture was concentrated under reduced pressure, then diluted in water and adjusted to pH 4 with 1 M HCI. 2- Aminopyrimidine-5-carboxylic acid precipitated as a white solid, which was isolated by vacuum filtration (244 mg, 90%): 1H NMR (DMSO-c/6) delta: 12.73 (1 H, br s), 8.63 (2H, s), 7.44 (2H, br s).

The chemical industry reduces the impact on the environment during synthesis 308348-93-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2008/70150; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 696-82-2, 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 696-82-2, name is 2,4,6-Trifluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(1) 34.1 parts of H acid was dissolved in 200 parts of water,Add 10% sodium carbonate solution to adjust the pH to 7,Total dissolved, then 13.5 parts of trifluoropyrimidine at 20 C,Condensed at pH 5 for 3 to 4 hours,No H acid when the end point, obtained condensation products; (2) take 12.3 parts of para-amino-anisidine diazonium salt, and the condensation product obtained in step (1) at 15 C, a pH of 6Under the conditions of coupling reaction 5h, to give compound A.

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 696-82-2, 2,4,6-Trifluoropyrimidine.

Reference:
Patent; Jiangsu Demeike Chemical Co., Ltd.; Wang Xiaojun; (7 pag.)CN106398303; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-66-9 ,Some common heterocyclic compound, 22536-66-9, molecular formula is C5H4ClN3O, 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 261 N-[10,ll-dimethyl-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02’6]dodeca- l(12),6,8,10-tetraen-3-yl]-2-[(2-methoxyethyl)amino]pyrimidine-4-carboxamide (ABR 239626) To a stirred solution of 2-chloropyrimidine-4-carboxamide, available via a literature method: PCT Int. AppL, 2001068612 (330 mg, 2.08 mmol) in DMF (6 mL) was added methyl 3,3,3- trifiuoro-2-oxopropanoate (355 mu, 3.47 mmol) followed by pyridine (170 mu, 2.08 mmol) under nitrogen. The reaction was stirred at room temperature for 2 h. Thionyl chloride (150 mu, 2.08 mmol) was added at 0C. The reaction was stirred for 1 h at 0C and then concentrated. The residue was filtered through a short pad of silica, eluting with DCM, under nitrogen. The filtrate was concentrated, and the acyl intermediate that remained was dissolved in DMF (5 mL) under nitrogen. The solution of acyl intermediate was added to a solution of 5,6-dimethyl-lH-l ,3- benzodiazol-2 -amine (280 mg, 1.74 mmol) in DMF (8 mL) followed by triethylamine (280 2.08 mmol). The reaction mixture was stirred for a further 16 h and then concentrated. The residue was dissolved in EtOAc (50 mL) and washed with water (3 x 50 mL) and brine (2 x 50 mL) and then dried (MgSO_i), filtered and concentrated to afford 2-chloro-N-[10,l 1 -dimethyl-4- oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02,6]dodeca-l(12),6,8,10-tetraen-3- yl]pyrimidine-4-carboxamide. (260 mg, 15%). m/z = 424.95 (MH)+. A sealable tube was charged with a portion of 2-chloro-N-[10,l 1 -dimethyl-4-oxo-3- (trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02,6]dodeca-l(12),6,8,10-tetraen-3-yl]pyrimidine-4- carboxamide (250 mg, 0.35 mmol), 2-methoxyethan- 1 -amine (92 muL·, 1.06 mmol), K2C03 (150 mg, 1.06 mmol) and DMF (5 mL). The tube was flushed with nitrogen, sealed and stirred at 100C for 6 h. Then reaction mixture was concentrated and the resulting residue was diluted with EtOAc (20 mL) and water (20 mL). The aqueous phase was extracted with EtOAc (2 x 10 mL). The combined organic extracts were washed with 10 % citric acid (aq) (2 x 20 mL) and brine (20 mL) and then dried (MgS04), filtered and concentrated. The crude product was purified by automated reverse phase HPLC (low pH Method A) to afford the title compound as a white solid (50 mg, 31 %).

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. 22536-66-9, 2-Chloropyrimidine-4-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTIVE BIOTECH AB; WELLMAR, Ulf; LIBERG, David; EKBLAD, Maria; BAINBRIDGE, Marie; EAST, Stephen; HARGRAVE, Jonathan; PREVOST, Natacha; WO2015/177367; (2015); 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. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine, molecular formula is C5H5ClN2S, 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: 49844-90-8

A mixture of 4-chloro-2-(methylthio)pyrimidine (102.6 g, 0.639 mol), 3-phenyl-1H-pyrazole-4-carbaldehyde (100.0 g, 0.581 mol), potassium carbonate (160.5 g, 1.162 mol), and dimethylformamide (700 mL) was stirred at 40-50 for 2 hours. Purified water (1.6 L) was slowly added to the reaction mixture, which was then stirred at room temperature for 2 hours. The resulting solid was filtered and then driedinvacuoto obtain 154.0 g of the titled compound. (Yield: 89.5%[78]1H-NMR(400MHz, CDCl3) delta 10.10(s, 1H), 9.20(s,1H), 8.65(d, 1H), 7.84-7.86(m, 2H), 7.67-7.71(m, 3H), 2.65(s, 3H)

With the rapid development of chemical substances, we look forward to future research findings about 49844-90-8.

Reference:
Patent; YUHAN CORPORATION; OH, Sang-Ho; KHOO, Ja-Heouk; LIM, Jong-Chul; LEE, Doo-Byung; LEE, Jung-Ae; LEE, Jun-Sup; JU, Hyun; SHIN, Woo-Seob; JEON, Sang-Seol; (24 pag.)WO2019/22486; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 31519-62-7 ,Some common heterocyclic compound, 31519-62-7, molecular formula is C5H4N2O2, 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.

114. f+)-2-f(3.,4-trans)-4-methyl-l-fpyrimi(iine-2-carbonyl)pyrroli(iin-3- yl)-7-ftetrahvdro-2H-pyran-4-yl)imidazo[5,l- 1 [l,2,41triazin-4f3H -one [1073] To a stirred solution of (+)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l: ][l,2,4]triazin-4(3H)-one (75 mg, 0.24 mmol) in DMF (5 mL) were added EDCI (70 mg, 0.37 mmol), HOBt (50 mg, 0.37 mmol), DIPEA (95 mg, 0.74 mmol) and pyrimidine-2-carboxylic acid (40 mg, 0.32 mmol) at 0 C under inert atmosphere. The resulting reaction mixture was allowed to warm to room temperature and stirred for 8 h. The reaction mass was diluted with water (100 mL) and extracted with DCM (3 x 50 mL). Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford (+)-2-((3,4-trans)-4-methyl-l-(pyrimidine-2-carbonyl)pyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l: ][l,2,4]triazin-4(3H)-one (40 mg, 40%) as an off-white solid. 1H-NMR (DMSO d6, 400 MHz): delta 11.95 (bs, 1H), 8.97 (d, 2H), 6.69- 6.58 (m, 2H), 3.98-3.84 (m, 4H), 3.65-3.57 (m, 4H), 3.22-3.27 (m, 2H), 2.68-2.61 (m, 1H), 1.90-1.84 (m, 4H), 1.08 (d, 3H); Mass (ESI): 410 [M++l] LC-MS: 98.92%; 410.3 (M++l); (column; X-bridge C-18, (50×3.0 mm, 3.5mu); RT 1.85 min. 0.05% TFA in water: ACN; 0.8 ml/min); UPLC (purity): 98.76%; (column; Eclipse XDB C- 18, (150×4.6 mm, 5.0mu); RT 8.23 min. 5mM NH4OAc (Aq): ACN; 1.0 ml/min; Chiral HPLC: 99%, R, = 37.69 min (Chiralpak IA, 250 x 4.6mm, 5mu; mobile phase (A) n- Hexane (B) DCM:MeOH (80:20) (A: B : 80:20); flow Rate: 1.00 mL/min); Optical rotation [a]D2: +12.17 (c = 0.25, DCM). TLC: 10% MeOH/DCM (Rf: 0.5).

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. 31519-62-7, 2-Pyrimidinecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); 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.5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, molecular formula is C7H6Cl2N2, molecular weight is 189.04, as common compound, the synthetic route is as follows.category: pyrimidines

Intermediate 14; 2-Chloro-iV-( 1 -methyl- lH-imidazol-4-yl)-6,7-dihvdro-5H-cvclopentardlpyrimidin-4-amineA mixture of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine (321 mg, 1.70 mmol),DIPEA (0.89mL, 5.1 mmol) and 1 -methyl- lH-imidazol-4-amine (prepared from Intermediate 1 as described in the synthesis of Intermediate 10, 200 mg, 2.04 mmol) in EtOH (15 mL) was heated overnight at 700C. LCMS analysis indicated that the reaction was complete. The title product (350 mg) was obtained after filtration and was used in a subsequent step without any further purification.1H NMR (300 MHz, DMSO-J6) delta ppm 9.72 (s, 1 H), 7.46 (d, J=I .32 Hz, 1 H), 7.30 (d, J=I .51 Hz, 1 H), 3.67 (s, 3 H), 2.76 (m, 4 H), 2.02 (dq, J=7.72, 7.54 Hz, 2 H). LCMS: 250.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5466-43-3, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 26452-81-3, 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. 26452-81-3, name is 4-Chloro-6-methoxypyrimidine, molecular formula is C5H5ClN2O, 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 microwave vial containing 4-chloro-6-methoxypyrimidine (0.290 g, 2.007mmol), (5-chloro-2-fluorophenyl)boronic acid (0.35 g, 2.007 mmol) and Na2CO3 (0.2 13 g, 2.007 mmol) in DME (10 mL), EtOH (1.250 mL) and water (1.250 mL) was purged with N2 for several mm. Then PdC12(dppf)-CH2C12 adduct (0.082 g, 0.100 mmol) was added and the vial was capped. The reaction was heated in a microwave at 100 °C for 1h. The reaction mixture was then diluted with water and extracted with EtOAc. Theorganic layer was washed with brine and then concentrated to give an orange-brownresidue. Purification by normal phase chromatography gave 4-(5 -chloro-2-fluorophenyl)- 6-methoxypyrimidine (400 mg, 84percent yield) as white crystals.4-Chloro-2-(6-methoxypyrimidin-4-yl)aniline was synthesized according to theprocedure described in Intermediate 5, by replacing (5-chloro-2-fluorophenyl)boronic acid with 4-chloro-2-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)aniline. MS(ESI) m/z:236.3 (M+H). ?H NMR (400MHz, CDC13) oe 8.78 (s, 1H), 7.49 (d, J=2.4 Hz, 1H), 7.15 (dd, J=8.6, 2.4 Hz, 1H), 6.99 (d, J0.9 Hz, 1H), 6.66 (d, J=8.6 Hz, 1H), 4.02 (s, 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 26452-81-3, 4-Chloro-6-methoxypyrimidine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 287714-35-6, 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.287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate, molecular formula is C6H5ClN2O2, molecular weight is 172.57, as common compound, the synthetic route is as follows.

Methyl 2-chloropyrimidine-5-carboxylate (0.927 g, 5.37 mmol) was added to a mixture of tert-butyl piperazine-l-carboxylate (1 g, 5.37 mmol) and DIPEA (2.34 mL, 13.4 mmol) in DCM (10 mL) in a 20 mL vial (exotherm). The reaction was then stirred at room temperature (bath temp). After 40 min, additional DCM (5 mL) was added along with an aqueous solution of 10 wt% citric acid (45 mL). The layers were separated, and the aqueous layer was extracted with DCM (10 mL). The combined organic layers were dried (Na2S04), concentrated under reduced pressure, and dried under high vacuum, giving 1.74 g (100%) of the title compound as a pale yellow-tan solid. LC/MS: m/z 323.0 (M+H)+, RT=1.00 min H NMR (400MHz, DICHLOROMETHANE-d2) delta = 8.82 (s, 2H), 3.89 (d, 7=4.5 Hz, 4H), 3.85 (s, 3H), 3.49 (t, 7=4.9 Hz, 4H), 1.47 (s, 9H)

Statistics shows that 287714-35-6 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloropyrimidine-5-carboxylate.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HARLING, John David; NEIPP, Christopher E.; PENDRAK, Israil; SMITH, Ian Edward David; TERRELL, Lamont Roscoe; YOUNGMAN, Mark; (120 pag.)WO2017/46036; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 157335-97-2, 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 157335-97-2 as follows.

To a solution of 5-(furo[3,2-c]pyrid in-4-yloxy)-2-(4,4,5,5-tetramethyl-1 ,3,2-d ioxaborolan2-yl)benzyl acetate (C34)(82 mg, 0.20 mmol) in 1,4-dioxane (10 mL)were added 5-bromo-4,6- dimethylpyrimidine (41 mg, 0.22 mmol), potassium carbonate (83 mg, 0.6 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (44 mg, 0.060 mmcl) and water (5 drops) at room temperature. The reaction mixture was degassed with nitrogen for 5 minutes, thensubjected to microwave irradiation at 12000 for 50 minutes. After filtration of the reactionmixture, the filtrate was concentrated in vacuo; purification was carried out by preparative thinlayer chromatography to give the product. Yield: 28 mg, 0.072 mmol, 36%. LCMS m/z 389.9(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,157335-97-2, its application will become more common.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia