Tag: M.W:100-200

Electric Literature of 939986-65-9, 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.939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, molecular weight is 139.5425, as common compound, the synthetic route is as follows.

A mixture of 6-chloropyrimidine-4-carbonitrile (153 mg, 1.10 mmol), Nphenylpiperidine-4-carboxamide hydrochloride 1 (221 mg, 0.914 mmol), K2C03 (253 mg, 1.83 mmol), THF (5 mL), and DMF (4 mL) was stirred at RT for 16 h. The mixture was concentrated under reduced pressure. The residue was partitioned between water, brine, and EtOAc. The organic layer was separated and the aqueous layer re-extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to afford compound 2 (274 mg, 81%) as a white solid. LCMS Mass:308.0 (M+1).

Statistics shows that 939986-65-9 is playing an increasingly important role. we look forward to future research findings about 6-Chloropyrimidine-4-carbonitrile.

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference 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

Synthetic Route 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

Related Products 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

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.14080-56-9, name is Thieno[2,3-d]pyrimidin-4-amine, molecular formula is C6H5N3S, molecular weight is 151.19, as common compound, the synthetic route is as follows.Product Details of 14080-56-9

EXAMPLE 4 This Example illustrates the preparation of 4-isopropylaminothieno[2,3-d]pyrimidine (Compound No. 5) by an alternative procedure to that described in Examples 1 and 2. A mixture of sodium hydride (0.64 g, 100%), 4-aminothieno[2,3-d]pyrimidine (3.5 g) and dry dimethylformamide (25 ml) was stirred for fifteen minutes at <20, then treated with 2-iodopropane (3.5 ml). After stirring at <20 for ninety minutes, the reaction mixture was diluted with water and cooled in ice. The precipitate was washed with water, dried and recrystallized from acetonitrile to give the title compound (1.4 g, m.p. 225-6). At the same time, in my other blogs, there are other synthetic methods of this type of compound,14080-56-9, Thieno[2,3-d]pyrimidin-4-amine, and friends who are interested can also refer to it. Reference:
Patent; Imperial Chemical Industries Limited; US4146716; (1979); A;; ; Patent; ICI Australia Limited; US4196207; (1980); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 149849-92-3, 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.149849-92-3, name is 2-Chloropyrimidine-4-carboxylic acid, molecular formula is C5H3ClN2O2, molecular weight is 158.54, as common compound, the synthetic route is as follows.

Under nitrogen protection, 2-chloro-4-pyrimidinecarboxylic acid (16 mg, 0.10 mmol) was charged.4-(8-Amino-3-((1R,3S,4S)-2-azabicyclo[2.2.1]heptan-3-yl)imidazo[1,5-a]pyrazin-1-yl -N-(pyridin-2-yl)benzamide (43 mg, 0.10 mmol) and TEA (20 mg, 0.20 mmol) in 1 mL THFHBTU (57 mg, 0.15 mmol), the reaction mixture was stirred at room temperature overnight.After TLC showed that the reaction of the starting material was complete, the reaction was quenched with water and extracted with EA (5 mL×3).The organic phase was back-washed with saturated brine, dried over anhydrous Na 2SO 21mg of target compound,It is a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 149849-92-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chengdu Beite Pharmaceutical Co., Ltd.; Chengdu Hai Borui Pharmaceutical Co., Ltd.; Li Yingfu; Huang Haoxi; Liu Guanfeng; Chen Tonghun; Ren Junfeng; Yi Shoubing; Su Zhonghai; (49 pag.)CN108191871; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 1004-40-6, name is 6-Amino-4-hydroxy-2-mercaptopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 1004-40-6

General procedure: A mixture of 0.174 g of 3-methyl-1-phenyl-2-pyrazoline-5-one (1, 1.0 mmol), 0.150 g of 4-chlorobenzaldehyde (2,1 mmol), 0.160 g of 6-amino-2-thiouracil (3, 1 mmol) and 9.8 mm3 of piperidine as a catalyst (10%) in 8 cm3 of ethanol in a 100-cm3 round-bottomed flask fitted with areflux condenser was heated with stirring in an oil bath maintained at 80 C. After the complete appearance of the white solid and monitored by TLC, the reaction mixture was cooled to room temperature and resulting solid product was filtered, washed with ethanol to give products 4a-4r.

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, 1004-40-6, 6-Amino-4-hydroxy-2-mercaptopyrimidine.

Reference:
Article; Bayat, Mohammad; Nasri, Shima; Mohammadali, Mohammad Reza; Monatshefte fur Chemie; vol. 148; 10; (2017); p. 1833 – 1842;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 156-81-0, Pyrimidine-2,4-diamine, 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 Pyrimidine-2,4-diamine, blongs to pyrimidines compound. Quality Control of Pyrimidine-2,4-diamine

General procedure: Vilsmeier reagent was prepared by mixing ice-cold dry DMF (50 ml) and POCl3 (30.0 mmol, 2.8 ml). The mixture was stirred for 15 min at 25 C. To the previous mixture, aminopyrimidines (10.0 mmol) in dry DMF (5.0 ml) were added over a period of 15 min at 0-5 C. The reaction mixturewas stirred for 24 h at 25 C.The mixture was then added to cold, saturated aq. K2CO3 andextracted with diethyl ether. The organic layer was washed withwater, dried over anhydrous Na2SO4, and evaporated underreduced pressure to afford the crude product, whichwas purified ina silica gel column chromatography using hexane/ethyl acetate(9:1) as an eluent to give the title compounds 2 and 8. 4.3.1. 2,4-Diaminopyrimidine-5-carbaldehyde (2) Brown powder, yield 59%; 1H-NMR [DMSO-d6, 400 MHz]: (delta,ppm) 7.10 (d, 2H, NH2, exchange with D2O), 7.52 (d, 2H, NH2, exchangewith D2O), 8.32 (s, 1H, H6-pyrimidine), 9.45 (CHO); 13C NMR[DMSO-d6, 100 MHz]: (delta, ppm) 106.2 (C5-pyrimidine), 162.7(C4-pyrimidine), 164.4 (C6-pyrimidine), 167.0 (C2-pyrimidine),189.5 (CHO).

The synthetic route of 156-81-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; AlNeyadi, Shaikha S.; Salem, Alaa A.; Ghattas, Mohammad A.; Atatreh, Noor; Abdou, Ibrahim M.; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 270 – 282;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia