Pyrimidines

Synthetic Route of 51940-64-8, 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. 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, molecular formula is C7H6Cl2N2O2, 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.

DIPEA (4.28 mL, 24.5 mmol) was added dropwise to ethyl 2,4-dichloropyrimidine-5- carboxylate (2.46 g, 11.1 mmol) and 4-amino-4-methyl-cyclohexanol hydrochloride (2.00 g, 11.1 mmol) in acetonitrile (40 mL) at 0C over 5 min. The reaction mixture was allowed to warm to rt, then was stirred at rt for 6 h and concentrated in vacuo, diluted with EtOAc (300 mL) and washed with sat. brine (100 mL x 2). The organic layer was isolated and dried over MgSC and concentrated in vacuo. The resulting crude product was purified by fee, elution gradient 0 to 20% EtOAc in n-heptane, to afford the title compound (2.82 g, 81%) as a pale yellow gum;lH NMR (400 MHz, DMSO) 1.36 – 1.44 (3H, m), 1.44 – 1.58 (6H, m), 1.57 – 1.71 (1H, m), 1.72 – 2.13 (3H, m), 2.41 – 2.54 (2H, m), 3.63 – 3.75 (1H, m), 4.36 (2H, q), 8.52 – 8.59 (1H, m), 8.67 (1H, d); mJz MH+314.

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 51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; TING, Attilla, Kuan, Tsuei; (103 pag.)WO2018/114999; (2018); A1;,
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Pyrimidine – Wikipedia

Related Products of 153435-63-3, Adding some certain compound to certain chemical reactions, such as: 153435-63-3, name is 2-(Tributylstannyl)pyrimidine,molecular formula is C16H30N2Sn, 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 153435-63-3.

A solution of 2-tributylstannanyl pyrimidine (390 mg, 1.05 mmol) , 2-pyrimidin triflate intermediate (13) (510 mg, 0.81 mmol), and Pd(PPh3)4 (95 mg, 0.081 mmol) in dry dimethylacetamide (7.5 mL) was heated at 130C for 6 h. After being cooled to room temperature, the reaction was filtered through a plug of Celite, the filtrate was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, solvent was removed and the residue was purified by silica gel chromatography furnishing the desired compound as a pale yellow solid (357 mg, 79 %) . The crude bosentan was further purified by recrystallization in hot ?0 / EtOH affording pure bosentan monohydrate (1) as a white solid (327 mg, 70 %) .^-RMN (200 MHz, d6-DMSO) : 1.29 (s, 9H) ; 3.85 (m, 2H) ; 3.93 (s, 3H) ; 4.59 (m, 2H) ; 6.81-7.18 (m, 4H) , 7.43 (d, J = 8.0 Hz, 3H) ; 8.45 (d, J = 8.0 Hz, 2H) ; 9.01 (s, 2H) ppm.DSC-TG: endothermic peak at 116.53 C, with a loss of weight of 3.1 % (monohydrate) . Dio : 1.36 um, D50 : 20.32 muiotaeta, D90 : 56.64 muiotaeta

According to the analysis of related databases, 153435-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LABORATORIOS LESVI, S.L.; RODRIGUEZ ROPERO, Sergio; HUGUET CLOTET, Juan; WO2011/117143; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 353272-15-8, 6-Chloro-5-iodopyrimidin-4-amine, 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 6-Chloro-5-iodopyrimidin-4-amine, blongs to pyrimidines compound. Quality Control of 6-Chloro-5-iodopyrimidin-4-amine

Compound (S)-3-(1-Aminoethyl)-2-cyclopropyl-8-fluoroisoquinolin-1(2H)-one (425 mg, 1.726 mmol),6-chloro-5-iodopyrimidine-4-amine (463.8 mg, 1.816 mmol) andA mixture of DIPEA (445.5 mg, 3.447 mmol) in n-butanol (2.5 mL) was heated to 130 C and stirring was continued for 30 hours.After cooling to room temperature and concentrating under reduced pressure, EtOAc m.The crude product was purified by silica gel column chromatography (EtOAc/EtOAc)The title compound was obtained as a pale yellow solid (250 mg, 31%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,353272-15-8, 6-Chloro-5-iodopyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wang Tingjin; Wu Weibin; (84 pag.)CN105130966; (2019); B;,
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Reference of 18592-13-7, 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 18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The respective halomethyl derivatives {6-(chloromethyl)uracil (0.1150g, 0.716mmol) or 4-bromomethyl-7-methoxycoumarin (0.1928g, 0.716mmol)} were suspended in acetone (1.5cm3) and then added individually to alkaline mixtures comprised of NaOH (0.0286g, 0.716mmol) in distilled water (1cm3). Upon dissolution of the organic precursors, the corresponding solutions were introduce in a dropwise manner to particular reaction mixtures of di(2-picolyl)amine (0.1001g, 0.5024mmol) and K2CO3 (0.069g, 0.5018mmol) in acetone (4.0cm3). Thereafter, the resultant reaction mixtures were heated at reflux for 24h, which was followed by the reduction of the solvent under vacuum. The respective residues were dispersed in separate 1:1 (v:v) water and chloroform combinations. Then the crude individual oily products were attained by the triplicate extractions from the aqueous mixture using chloroform and these extracts were dried over anhydrous MgSO4 prior to removing the solvent under reduced pressure. The relating crude products were purified by column chromatography using a silica stationary phase and DCM: MeOH (v:v, 9:1) as a mobile phase. 2.2.2 6-((bis(pyridin-2-ylmethyl)amino)methyl)uracil (Hurdpa) X-ray quality single crystals were grown via the slow diffusion of n-hexane into a solution of dichloromethane. Yield: 0.72g (51%). Molecular mass (m/z): Cald. for C17H17N5O2: 323.14. Found: 346.13 [M+Na]+ (Fig. S3). FTIR (cm-1): v(N-H) 3370 (br, w); v(C=O) 1681 (vs); v(C=N) 1579 (s); v(C-N) 1161, 1136 (m). 1H NMR (d6-DMSO/ppm/298K, Fig. S4): 11.04 (br, s, 1H, N5H); 10.87 (s, 1H, N4H); 8.55-8.50 (m, 2H, H1, H12); 7.84-7.75 (m, 2H, H3, H10); 7.52-7.46 (m, 2H, H2, H11); 7.33-7.24 (m, 2H, H4, H9); 5.57 (s, 1H, H17); 3.90-3.83 (m, 4H, H6, H6?, H7, H7?); 3.52 (br, s, 2H, H13, H13?). UV-Vis (MeOH, lambdamax (epsilon, M-1cm-1)): 256nm (sh, 1540); 262nm (1720); 268nm (sh, 1350); 359nm (10)

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 18592-13-7, 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione.

Reference:
Article; Gramni, Larusha; Vukea, Nyeleti; Chakraborty, Abir; Samson, William John; Dingle, Laura Margaret Kirkpartick; Xulu, Bheki; de la Mare, Jo-Anne; Edkins, Adrienne Lesley; Booysen, Irvin Noel; Inorganica Chimica Acta; vol. 492; (2019); p. 98 – 107;,
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Synthetic Route of 2227-98-7, 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 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 17.4: (3f?,4S)-4-Butyl-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxypyrrolidine (20, R = Et); Formaldehyde (86 mul_, 1.1 mmol, 37 wt% solution in water) followed by 9-deazaadenine (112 mg, 0.84 mmol) are added to a solution of 19 (R = Et) (100 mg, 0.56 mmol) in 1 ,4-dioxane (1 mL) and water (2 ml_). The reaction mixture is warmed to 85 0C and after 1 h the crude reaction mixture absorbed onto silica and eluted down a silica column using a gradient 5 – 30% (7 N NH3 in MeOH) in CH2CI2. The crude product is collected, concentrated and subjected to flash chromatography (5 : 4.5 : 0.5, CH2CI2 : MeOH : 28% aq. NH4OH) to afford 20 (R = Et) as an off- white solid (90 mg, 56%). 1H NMR (500 MHz, CD3OD): delta = 8.17 (s, 1H), 7.49 (s, 1H), 3.86 – 3.83 (m, 1 H), 3.81 (q, J = 13.2 Hz, 2H), 3.05 (dd, J = 9.6, 8.0 Hz, 1H), 2.74 (dd, J = 10.4, 6.3 Hz, 1 H), 2.69 (dd, J = 10.4, 4.0 Hz, 1H), 2.17 (dd, J = 9.7, 8.0 Hz. 1H), 1.98 – 1.90 (m, 1H), 1.57 – 1.47 (m, 1H), 1.34 – 1.24 (m, 5H) and 0.89 ppm (t, J = 6.9 Hz, 3H). 13C NMR (125 MHz, CD3OD): delta = 152.1 , 151.0, 147.0, 130.1 , 115.1, 112.6, 77.8, 62.4, 59.7, 49.1 , 48.6, 34.0, 31.5, 23.8 and 14.4 ppm. ESI-HRMS for C15H24N5O [MH]+ calcd, 290.1981; found, 290.1988

According to the analysis of related databases, 2227-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBERT EINSTEIN COLLEGE OF YESHIVA UNIVERSITY; INDUSTRIAL RESEARCH LIMITED; EVANS, Gary Brian; LONGSHAW, Alistair Ian; SCHRAMM, Vern L.; TYLER, Peter, Charles; WO2011/8110; (2011); A1;,
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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. 155-12-4, name is 2-Chloro-5-fluoropyrimidin-4-one, molecular formula is C4H2ClFN2O, 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. Computed Properties of C4H2ClFN2O

Example 1b 2-(2-Chloro-5-fluoro-6-oxo-6H-pyrimidin-1-ylmethyl)-benzonitrile The title compound was prepared in 44% yield from 2-chloro-5-fluoro-3H-pyrimidin-4-one as described in U.S. patent application Ser. No. 10/918,317. Specifically, 5-Fluoro-2-chloro-3H-pyrimidin-4-one was stirred in DME/DMF under nitrogen at 0 C. Sodium hydride (95%) was added in portions. After 10 min, lithium bromide was added and the reaction stirred at r.t. alpha-Bromo-o-tolunitrile was added, and the reaction stirred at 65 C. for 8 h. The solution was diluted with EtOAc, washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography (1:1:1 EtOAc/hexanes/CHCl3) gave the title compound. Also obtained from the reaction were impure fractions of the less polar O-alkylated isomer, and the more polar N3-alkylated isomer. 1H NMR (400 MHz, CDCl3): delta 7.81 (s, 1H), 7.74 (dd, 1H, J=7.6, 1.2 Hz), 7.59 (td, 1H, J=7.6, 1.2 Hz), 7.45 (t, 1H, J=7.6 Hz), 7.15 (d, 1H, J=7.6 Hz), 5.67 (s, 2H). MS (ES) [m+H] calc’d for C12H7N3OFCl, 264, 266; found 264, 266.

With the rapid development of chemical substances, we look forward to future research findings about 155-12-4.

Reference:
Patent; Chyall, Leonard J.; Lorimer, Keith; McClausland, Linda J.; US2007/66636; (2007); A1;,
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Pyrimidine – Wikipedia

Application of 7431-45-0, Adding some certain compound to certain chemical reactions, such as: 7431-45-0, name is 2-Phenylpyrimidine,molecular formula is C10H8N2, 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 7431-45-0.

General procedure: In a Schlenk tube, a solution of R3In (0.375 mmol, ~0.3M en THF) and the arylpyridine (0.25 mmol)were successively added to a solution of Rh(PPh3)3Cl (24 mg, 0.025 mmol) in chlorobenzene (20 mL).The mixture was stirred at 120 C during 48 h, and the reaction quenched by addition of dropsof MeOH. The solvent was evaporated and CHCl3 (25 mL) was added. The organic phase waswashed with aq. NH3 (5%, 15 mL), dried, filtered, and concentrated. The crude was purified by flash chromatography (Et2O/hexane) affording, after concentration and drying, the cross-coupling products.

According to the analysis of related databases, 7431-45-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Riveiros, Ricardo; Tato, Ruben; Sestelo, Jose Perez; Sarandeses, Luis A; Molecules; vol. 23; 7; (2018);,
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Application of 18740-39-1, 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 18740-39-1 as follows.

4-hydroxy-3,5-dimethylbenzonitrile (0.15 g, 1 mmol) and potassium carbonate (0.17 g, 1.2 mmol) were weighed in 5 mLN, N-dimethylformamide (DMF), stirred at room temperature for 15 minutes, and then 2,4-dichlorothieno [2,3-d] pyrimidine(0.21 g, 1 mmol) was added at room temperature for 2 h (TLC detection reaction was complete). At this point there is a lot of white solid generated, slowly To this was added 25 mL of ice water, filtered and dried in a vacuum oven to give the white solid as compound 4 – ((2-chlorothiophene[2,3-d] pyrimidin-4-yl) oxy) -3,5-dimethylbenzonitrile in a yield of 91.7percent

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18740-39-1, its application will become more common.

Reference:
Patent; Shandong University; Liu Xinyong; Kang Dongwei; Zhan Peng; Wu Gaoshan; Huo Zhipeng; (22 pag.)CN106866699; (2017); A;,
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Synthetic Route of 14080-23-0 ,Some common heterocyclic compound, 14080-23-0, molecular formula is C5H3N3, 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.

Pyrimidine-2-carboxylic acid (11):To a stirred solution of pyrimidine-2-carbonitrile (10) (201 mg, 1.914 mmol) in water (5 mL), KOH (214.3 mg, 3.83 mmol) was added and the reaction was refluxed for 3 h. After consumption of the starting material (by TLC), the reaction was slowly brought to RT, neutralized with 2N HC1 and water was removed from the reaction mixture to give the crude residue which was extracted with EtOAc. The combined organic extracts were filtered through a pad of celite and the filtrate was concentrated under reduced pressure to provide compound 11 (84 mg, 35.4%) which was carried for the next step without any purification.TLC: 80% EtOAc/Hexane (Rf: 0.05)1H NMR (400MHz, CD3OD-d4): delta 8.83 (br s, 2H), 7.47 (t, J = 4.8 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14080-23-0, its application will become more common.

Reference:
Patent; THERACRINE, INC.; SUN, Lijun; BARSOUM, James; WESTER, Ronald; WO2013/13238; (2013); A2;,
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Pyrimidine – Wikipedia

Electric Literature of 10244-24-3, 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. 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, molecular formula is C12H17ClN4O2, 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.

Reference Example 13 2,6-Di-morphoIin-4-yl-f4<5'lbipyrimidinvI-2'-ylamineTo a cold solution of 2,4,6-trichloropyrimidine (16g) in methanol (20OmL) was added morpholine (15.2ml). The reaction mixture was stirred for 24 hours and the solvent was then removed in vacuo. The residue was dissolved in dichloromethane, washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 4-(6-chloro-2-morpholin-l-yl-pyrimidin-4- yl)-morpholine.Reaction of 4-(6-chloro-2-morpholin-l-yl-pyrimidin-4-yl)-morpholine with 2- aminopyrimidine-5-boronic acid, pinacol ester using standard Suzuki conditions yielded the desired title compound. 400MHz IH NMR CDC133.64-3.66 (m, 4H, 2 x CH2), 3.7-3.86 (m, 12H, 6 x CH2), 5.22 (sbr, 2H, NH2), 6.17 (s,H, ArH), 8.89 (s, 2H, 2 x ArH).

According to the analysis of related databases, 10244-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; WO2009/66084; (2009); A1;,
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Pyrimidine – Wikipedia